Sex With Son's Teachers

by Anonymous on Oct 1, 2020 at 3:39 PM

Was it a one time thing or did you have to have additional meetings with the pair of them to keep your son in the school you wanted him in?

If you had additional meetings, did either of them ever manage to make you cum? Were either of them bigger and-or better at fucking you than your husband?

Did either of them ever request oral? That you swallow?

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by Anonymous on Oct 1, 2020 at 8:43 PM

My confession was for the first time but since then it feels more like I am cheating on my husband than doing something special for my son.

I don't want to do any of it but they have helped him and there's no talk of him going to the "hood" school for classes.

I usually have sex with his teacher by sitting or kneeling on his lap. We meet in a parking lot every week. He parks his SUV next to mine and we do it in the back seat of mine as it is larger. We haven't figured out a better way to meet every week than on Saturday mornings when I can tell my husband I'm doing groceries after the gym. We actually meet before the gym so I can shower after sex. IF I miss a meeting, he tells me we have to make it up. It happened once and I made it up in the Target parking lot while my husband watched Sunday football at home. I hope I can stop seeing him at the end of the year.

I have to meet with the specialist once a week, too. We can meet in his office where there are no windows and it is located in a quiet area of the school. I have to wear skirts or dresses and not wear underwear. The specialist is younger so he wants oral both ways (we have to pleasure each other orally), then sex is usually from behind at his desk. He recently asked me for anal but I have a hard time with that so he seemed to lose interest. I assume that so long as my son needs help and stays at this school I will be seeing the learning specialist.

Yes, I orgasm with both men.

Happy?

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by Anonymous on Oct 1, 2020 at 9:04 PM

Nicely detailed answers; so, yes, I'm happy.

A couple of things I'd appreciate a little more information on:

As was asked before, are either or both of the teachers better hung than your husband?

Assuming he takes you without a condom, how do you keep from leaking sperm down your thighs when you leave his office?

About how many weeks has school been in session? Or more directly, how many times have you serviced each of them? Do you give them oral after they fuck you so they can return home with their cocks clean?

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by Anonymous on Oct 2, 2020 at 6:14 AM

I could not post again from my phone, but could from my laptop. I don’t know how many times I can post.

I am not sure that either man is bigger than my husband, though the learning specialist seems to go deeper than what I’m used to. My son’s teacher is uncircumcised, and I think he feels a little better, as though he can pump in and out with less friction while we have sex.

Having to go without underwear, I have problems with leaking after meeting with the specialist. I swallow some of his first orgasm so usually his second time is a smaller amount, but twice so far it felt like he went forever. I had to meet a friend last week for coffee after meeting with the specialist. She told me I had a stain on the back of my t-shirt dress and I figured out that it was from sex. My friend didn’t say anything, but I am sure she knew what it was and I hope she thinks it was from my husband. It does go down my thighs, but it depends if I can wipe up with tissues after we’re done. He has a box of tissues, but twice already he has run out. The teacher and I meet on Saturdays before the gym. The crotch of my yoga shorts is usually wet but I don’t think anyone notices.

School started on August 21. My first meeting with the two men was September 2. I left so fast that my son’s teacher emailed me an invite to a follow-up meeting in the learning specialist’s office on September 4. I learned later that the specialist’s office is quiet and away from other classrooms and offices. When we met that Friday, the teacher came to the office and we sat together to talk about my son for a few minutes. Then the specialist said, “Now, about our arrangement.” They told me they wanted to see me once a week but that it would be hard for them given their schedules to meet me together. I had on jeans and the specialist said I should wear skirts and dresses, as short as I could go. He said that I had great legs being so tall (five foot nine inches) and they wanted to see them. I wore leggings with underwear once so far, and the specialist gave me a warning. We talked for a few minutes and came up with the plans I described before. Then the teacher said he had to get back to class and that we should have sex before he goes. They had me stand up and pull down my jeans and underwear. I had to give oral to the specialist while the teacher was behind me. Since then we have met every week including this one, so it has been five weeks, six times with each man if you count September 2 and 4.

I am not a dumb bimbo. I have a college degree. My husband does really well so I can focus my time on our son, our home, staying in shape and volunteering. I really want what is best for my son. I fully realize what I am doing is stupid. Probably most mothers would not do it, but in that moment during the first meeting I realized it was a way I could control what happened for my son rather than relying on the system or having him treated like a lab rat in tests. I could get both men in so much trouble so easily, but then I am not sure what would happen to my son, and they know that.

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by Anonymous on Oct 2, 2020 at 7:40 AM

If you change devices and IP addresses, you can comment once from each as Anonymous. On the other hand, if you log in as "Less than Perfect Mom" like you did for the original confession, you should be able to comment an unlimited number of times.

Since you claim to orgasm with both men, have you started looking forward to visiting them? Do you get wet in anticipation of getting your extramarital fucks for the week from your son's educators?

Does the mindset ever kick in and you feel like a whore? Like you're trading access to your c**t for something you value? Did it seem even more so when the specialist was trying to work his cock up your ass? Have you ever let your husband claim that hole? Or was the specialist devirginizing that opening?

On the subject of your visits with the specialist, you said you swallow most of his first orgasm. Do you mean to imply that he fucks you to completion twice on each visit? Or is the first one oral only? When you give him head, does he insist you be in the subservient position on your knees?

Speaking of his demand you go commando during your visits, have you considered carrying a pair of panties in your purse so you can put them on in the women's room after he seeds you? Or is the thrill of having him run down your thighs part of the sexual high you get from being used?

You either missed or ignored one question I had in the last note. Do you orally clean your juices off of their cocks when they finish fucking you so they can go about the rest of their day without your pussy smell getting wiped all over their underwear?

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by nunya on Oct 2, 2020 at 7:54 AM

I thought I'd delurk for a minute and ask about something you closed your original confession with. You said you thanked them at the end of the first meeting where you got fucked.

Did you orgasm during that first encounter? If you did, and it was obvious, do you have any idea whether they took your "thank you" as acknowledgement of the favor they were doing for you with regards to your son or whether they took it as thanks for working over your pussy and giving you an orgasm?

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by Anonymous on Oct 2, 2020 at 9:47 AM

I wasn’t expecting so many questions, but it does make what is happening feel more normal to talk about it.

Yes, I do orgasm with both men. I orgasm fairly easily from what I know from talking with my friends. I do not look forward to this, I just know it is something I have to do. I guess I do get wet thinking about it as I go to each meeting, though more so with the specialist than with the teacher. I don’t know that I am turned on by this, but if I think about previous times on my way to one of these meetings, my puss does get aroused and pulses. That really does sound so terrible considering I’m happily married.

Yes, I feel like a slut or a whore. I think “slut”. I don’t like anal that much. I tried it in college. My husband has never asked about it, but he does rub and pat my ass. The specialist wanted to try it so we did. I was so awkward about it that it wasn’t very good. He couldn’t get in as deep as he tried to but we also didn’t have lube. This week he never asked about anal.

The specialist is younger than me while the teacher is much older. He ejaculates twice each time we meet, at least so far. Usually he eats out my puss before he is ready to go the second time. I am pretty sure eating me out is a huge turn-on for him and gets him horny for sex. For oral, I don’t know that I considered being on my knees a subservient position, but that is how I do it.

This will sound like I’m really stupid. Until you asked, I never thought about taking along panties. I don’t know if that is what he intended. I think he wants me to go commando all the time. No, I only go commando to get rid of VPL. Again, I am doing this for my son, so I see it as having sex for him rather than being sexy, if that makes sense. I’m not stupid, I know that it feels naughty to have semen running down my legs. It’s just part of what I have to do.

No, I do not lick them after sex. The teacher uses my panties to wipe off since we know I will change them when I take my shower. I don’t exercise in thongs, so they are normal panties with a back we can use to wipe with. The specialist uses tissues or just puts it away, so I guess maybe he still smells like sex.

Yes, I did orgasm at the first conference. I never thought about saying thank you meaning anything other than thanking them for helping my son. Seriously, I am sure they knew that.

So one funny thing that I can’t get out of my head. You asked about the panties. The whole time I am responding I keep thinking about your question and I have this compulsion to ask the specialist if I can. I’m just realizing how weird that is. The specialist is definitely assertive, but I didn’t think of just how much I’m doing as he tells me. LOL – I will still ask him.

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by Anonymous on Oct 2, 2020 at 9:52 AM

So I could post, but it doesn't use my name (the name I signed on with). What does that mean?

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by Anonymous on Oct 2, 2020 at 10:05 AM

u got my thick cock hard, wanna eat ur dirty pussy n fuck u good

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by nunya on Oct 2, 2020 at 10:25 AM

You may not think of it as looking forward to it like some kind of treat, but your pussy is definitely anticipating - in a good way - of getting a workout if it gets wet when you think about servicing them.

More stray questions your tale has brought to mind. Had you ever had two men all at once or serially back to back before these two? I know many women get adventurous in college, so had you experienced an MFM threesome with spit roasting [one in the pussy and one in the mouth] during your wild days?

A couple of things you might want to consider with the specialist. First, he probably already thinks you're carrying panties in your purse or car to put on after he loads you up. If you alert him to the fact that you aren't and sometimes get embarrassed by all the cum rolling down your thighs, he'll deny you permission to start as sure as the sun rises in the east. He'll get off on the idea that he's been controlling you beyond the walls of his office.

Second, if you carry a purse to your meetings with him, put a small tube of lubricant in there. KY, moisturizer, petroleum jelly, whatever. Just because he didn't ask for anal two weeks in a row doesn't mean he's gone completely off the idea. As with the panties, don't mention it to him. If you do he'll take it as a sign that you're prepared for him to try again to loosen up your rear hole and fuck it deep.

So, for the first ejaculation, does he fuck you for a while then pull out so you can finish him with your mouth? If that's the case, are you already wet and ready for him to enter you without additional foreplay? If he plows ahead and cums in you the first time, does he still eat your pussy before he fucks you the second time? Do you swallow when he cums in your mouth?

Going back to the first conference for a second, did you orgasm for men or just one?

Does the uncircumsized one ever ask you for oral?

Do you often end up fucking your husband on Saturday nights with some small portion of your backseat lover still in your pussy? Has your husband ever eaten you out on a Saturday night when you didn't feel completely clean after taking your pre-gym load?

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by nunya on Oct 2, 2020 at 10:40 AM

One last thing while it's rattling around in my head, does the specialists' ban on underwear extend to your bra as well? Whether it does or not, can I get you to share what size bra it is that you do or do not get to keep on for visits to his office?

I do not have a clue, by the way, on why it changed your posted name to "Reacher" but I've come to suspect it's some kind of default setting since it's so common on the board.

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by Anonymous on Oct 2, 2020 at 11:04 AM

So I take it you are home and online during the day? I need to get a few things done around the house before my son gets home, but obviously I checked to see if you responded. Can you tell me why I’m called Reacher instead of my login? That sort of creeps me out like there’s a glitch and next thing I know my real name appears.

I’ll leave the “I really want it” issue alone for now. I do orgasm, but I don’t dream about these men all week long or anything like that. Believe me, there is no forgetting how slutty I feel!

Yes, I was wilder in college before I met my now-husband. I’m a sorority sister, or was, and we had a lot of wild parties. I wasn’t the wildest one, but I did have two guys at once a few times. I didn’t know it was called spit roasting, but I get it.

I’m a little confused by your ejaculation question. With the specialist, it has been oral first, then sex. I blow him, he eats me, he penetrates me. The only time that was different was when we tried anal. He came in me when we tried but he said it didn’t feel very good. He made me suck on him so that I “didn’t leave on a bad note.” (his words). We didn’t have regular sex that time. Yes I do swallow what I can, but usually some escapes and lands on the floor.

I orgasmed for both men. No, my son’s teacher is a little older and I think he’s just happy to be having sex, so he hasn’t asked for oral. I guess I would do it if he asks, but fortunately that has not come up.

I guess there may be some of their sperm in me when I have sex with my husband. I take showers or clean up afterwards, but I would imagine there is still something in me from before. My husband doesn’t eat my puss. That’s not his thing.

5 foot 9 inches, 34C, 130-ish pounds…but not 140 if I can help it! I always wear a bra unless I'm at home.

Ok, I have to go. Thanks for talking with me about this. It feels really good just to get it all out and talk about it. Well, type about it.

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by nunya on Oct 2, 2020 at 12:34 PM

More so now than usually. I'm in a slow period and keeping your story open in a hidden tab. I pop in and refresh every little bit to see if there is anything new.

I suspect if you dig really deep in those feelings of anticipation, there is pressure being put on one of your motivational buttons. You're a 33 year old MILF. Being "forced" to service these two men in positions of authority who have a lot to lose if word gets out is no doubt giving you a little thrill down your spine. You're feeling submissive, but very, very attractive. You've reeled in both of these men with your looks and desperation. You've not had two men want you so badly that they'll share your holes instead of waiting in line since college - pre-marriage, pre-kid, pre-responsibility. Those thoughts might be hidden even from yourself, but they are the source of those wet, swollen pussy lips that are waiting to be spread by your abusers. Dig a little deeper, and I think you'll find the specialist at the center of this. Here's a man younger than you who is demanding and always drops two loads of sperm in you when you meet.

Sorry for the confusion on the ejaculation question. When it was first brought up you mentioned swallowing most of his first cum and missed the line where you spoke of giving each other oral to start things off. My bad.

Of course, one other thing comes to mind. If oral isn't your husband's thing, you may get wet anticipating the specialist giving you head.

34C is a very respectable rack. Do either of the men ever push your bra up or take it off completely so they can play with your tits? Or are they typically in too much of a hurry to bother?

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by Anonymous on Oct 4, 2020 at 1:27 AM

I'm a father. My daughter struggled in a college class and is retaking it. She picked a fairly good looking professor...not George Clooney, but decent. I suggested she schedule time with the professor and start having sex with him. I said that she'll have to solve her own problems in the real world, and for her sex will be the easier route. We don't go into every detail, but over coffee she's told me she is sucking or fucking him every week now in exchange for a guaranteed B, but has to earn an A. I told her to expect a B and just consider it a bonus if she gets the A.

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by nunya on Oct 5, 2020 at 6:31 AM

Did the teacher give you a good dicking over the weekend? He make you cum? Leave a big load in your married pussy?

So I'm curious, are either of these guys married as well? Are you servicing the needy or the greedy as the old joke goes?

Will the identity of your son's teacher will change in the next academic year? I get the idea from what you wrote that the specialist is some kind of program overseer and you'll probably have to deal with him the whole time your son is in the school. Assuming your son advances to the next level, does he get a new teacher or are they paired for the duration?

If he does get a new teacher, do you think the specialist will reach out to him to share you or will he up his demand to two meetings per week? What if your son's new teacher was female and wanted weekly oral service. Would you consider it?

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by Anonymous on Oct 5, 2020 at 1:11 PM

Okay, this really isn't something I'll do every day, though it is sort of fun and dirty to relive it this way. Everything about this feels like it will spiral out of control. I'm saying it's "fun" to relive it but I a mortified slut praying for it to end.

From the other day, I understand what you say about having power relative to both men, but at the same time I feel like I lose that power when I think about my son and him being transferred off to the crappy school because I couldn’t keep my mouth shut. I know this all sounds degrading to me, but I feel like this is something I can do for him as his mother. I will say I’m generally quiet and fairly laid back unless I’m with friends or really relaxed. My friends tell me I can be a doormat when it comes to volunteer organizations and people saying how they want things even if I’m doing more of the actual work. I know I lack confidence versus a few years ago when I was working and contributing myself.

Yes from the other day, both men grab my breasts constantly or pull them out of my bra underneath my shirt or dress. The teacher mostly holds them I guess, whereas the specialist squeezes and kneads. And yes, the teacher is married. The specialist is single.

I’m a little upset because today I was called by the school and asked to meet with the specialist. We usually meet mid-week. I’m not stupid, so I’m curious what is going on…we met today, now we’re meeting on Friday because he said it worked in his schedule. Even I’m not dumb enough to believe he won’t have me come in next week, but not exactly like I can get out the contract and argue.

So, I did go in knowing he’d like my outfit. I purposely wore a suede shirt dress I just bought from A&F. He really liked the dress, a LOT. He had me sit on his desk so he could give me oral. We still had sex, but he didn’t last long. I guess if I had my way I’d want more days like this since I didn’t have to give much effort. Yea dress!!!

I didn’t just dress up for him by the way. I had a lunch for a charity after our meeting so I needed to look good. I could wear it to both places in case I didn’t have time to change, and I really didn’t. It was a little short for the luncheon because I could only find a size Small in regular length and I probably need tall, plus it’s tight on my hips, but it’s super cute. No one at the luncheon would say anything to me directly even if it was short…they’ll just snipe behind my back. I’m either a spoiled housewife with spare time on my hands to live at the gym or I’m a worthless bimbo living off my husband, or some combination of those. I’m used to it now. People who know me even tend to forget I’m certified in my field – yes, I really am, though not active. Anyway, I originally wanted to save the dress for a date night to a nice restaurant, so that’s the only bad thing is now I sort of spoiled it for myself.

You’re right that he has more sway over me, now that I have thought about it. I have to admit I didn’t take the advice from Friday. Today I asked him about wearing panties after we met and he said he couldn’t do anything about it, but he’d prefer I not. So in my little “smart girl dumb bimbo” way right now, I’m actually nervous I would screw something up if I wore underwear, so I’ll stick to going commando after my meetings with him. It’s completely illogical, but I feel better knowing I’m doing what he tells me to.

I also met with the teacher on Saturday. As he had sex with me, I leaned into him from off the seat and looked out the windows. It made me realize even more now that we’re in a strip mall at the back end of Home Depot and people drive by. I was looking out the front window the whole time thinking someone could look right in. They could see me fairly clearly through the front window if they tried. My back and side windows are deep tinted, but now I’m thinking about it more.

By the way, my son is doing well through all of this. The teacher is providing extra materials that my son and I work on at home. The specialist is working with him twice a week and formulating a plan where I could look into some one-on-one therapies that don’t involve sketchy schools and everyone labeling him “special.” To me that does make this worthwhile.

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by Anonymous on Oct 5, 2020 at 3:55 PM

I have to answer this quickly, but your question about "how long does this continue" really bothered me. So far as I know, my son gets a new teacher next year. Unfortunately, and the part that sort of upsets me now that I think about it, is that the specialist does continue (he is the only one for the school and there are more grades to go in this school) and if my my son still needs help, the specialist would be involved.

It's one thing for me to live in the moment of the sex. It's fine on its own in that if you enjoy sex and you're sneaking around you sort of come to terms with it, or at least I am. I'm trying not to enjoy it beyond the momentary climax, if that makes any sense...I don't want each experience to build into something more. The first time felt good and so have the others. But when I think of it in terms of my marriage and my life, I have a little trouble keeping it together. I don't want to lose what I have and I'd rather have my husband and son but I'd also rather have my son succeed here than be treated differently.

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by Anonymous on Oct 6, 2020 at 2:43 PM

Am I reading it right that the specialist expects to tap your married pussy twice this week? I mean, it looks like a very intentional power play on his part. He could just as easily told the contact person to let you know the Wednesday meeting had been moved to Friday. He must have had a disappointing weekend that didn't include getting his rocks off so he decided to use your open, wet c**t as his depository.

It also sounds like you didn't have to blow him yesterday. Probably just as well since I'm certain you wouldn't want to get your spit and his cum all over the front.

Since you mentioned the specialist holding sway over you, I have a question about his and the teacher's behavior toward you. Since the deal is explicitly based on the notion that they have you in a bind, are they ever verbally abusive; calling you a slut or whore, reminding you that you're giving up your married pussy, telling you to swallow when they cum in your mouth, or telling you generally to take it when they cum in you? Or one of the all time favorites, instructing you to name the bastard they hope to plant in you after your husband?

I guess there's a mild bit of physical abuse possible as well. Does the specialist ever hold your head to make sure you don't pull away as he cums? Do either hold you hips to insure they get to cum as deeply as possible in your pussy? Lightly slapping, firmly groping, and biting your tits? Pinching and twisting your nipples? Spanking your ass to a medium pink shade?

Speaking of your ass, have you purchased some lube to put in your purse in case anal comes up for discussion again?

I can understand your desire to keep each incident as a separate, sometimes [or frequently] pleasurable, incident, and not part of an ongoing affair over which you have no control. I have doubts you'll be able to keep that discernment viable as the situation progresses over 36 [or however many] weeks you have in the academic year.

While you seem to think the "slut" designation preferable at the moment, I question whether you'll be able to keep the detachment required to keep that mindset. I fear you'll come to breaking point where your internal morality will demand a reason you're acting like this that's more powerful than "it feels good," particularly if the specialist threatens to increase your weekly meetings. At that juncture, you'll search for justification and I'm afraid the spinning wheel stops on "whore" since the ultimate self justification is external to the sex and your relationship with your husband. I hope your affection for your son is strong enough to overcome whatever stigma you apply to yourself for breaking your wedding vows.

And, as you speculate, I think there is a very real chance the specialist will expect continued access to your curves and holes while your son is enrolled in the school.

You know, the speed with which the specialist and the teacher set this up makes me question whether they have done this before with other mothers in the program. In fact, I wonder how many "parent conferences" are on his weekly schedule.

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by Anonymous on Oct 7, 2020 at 7:07 AM

I was just thinking about this yesterday…I originally wanted to post something on cosmo’s sex stories pages, but decided that was just for juicy stories. So here I am working up to pretty much every juicy detail anyhow. Hope this is truly anonymous…or at least no one local is piecing this all together creeping around the Home Depot lot looking for my SUV on Saturdays. Guess what, it’s not a Home Depot! ;)

Going in order of your questions…

Friday’s meeting has me upset right now. I don’t know what is going on but going twice in one week is a bad idea in my mind. I should have said no to the Monday meeting but he was “working on his schedule” when we agreed to Monday. I am thinking this though…no matter how good I look, would he at some point lose a little interest? Something like diminishing returns over time but in this case the extra rounds makes each round less valuable or less interesting? That could be weeks or even a couple of months away, but won’t this get old…I’m the same woman every week? I’m already going commando and already bare pussy on him…whatever dress or skirt I do wear is pulled up or off within a few minutes so it’s the same body all the time. I’d get bored I think since it’s not like I’m his wife.

Neither man is abusive verbally. They do pound me pretty hard sometimes, and I do see stars with the specialist sometimes. The teacher is more gentle and consistent, very soft rhythmic movements versus usually harder pumps by the specialist. When I see the teacher it’s very unassuming. We park, get out of our cars so we can get in the back of my SUV and meanwhile he’s saying “Hi” and my name and I usually say “Hi” and call him by his last name. There’s usually a “How are you” in there for each of us, though it’s pretty meaningless until we get in the back and start stripping. With the specialist I am more timid or quiet I guess, and I start out with a typical “Hello”…I’m usually more apprehensive about what is going to happen next versus the teacher is pretty much steady when it comes to what he wants to do. No name calling, no degrading me by rubbing it all in my face. Obviously they cum in me and yes, I do mostly swallow the specialist then clean up the extra with tissues. From a pure sex perspective, it’s a little insane sometimes and sometimes more like a college fuck than mature sex.

Do they grab my hips or does the specialist hold my head…yes. I don’t have trouble orgasming, so I tend to grind or buck harder when I’m cumming. The specialist also pulled me backward by the hair the couple of times he’s taken me from behind. This is the really dirty part of it…when I’m doing it I am doing it. In the back of the SUV I can moan and scream a little, but we try to be really quiet at the school. When they go in me, I want to feel it deep so that I enjoy it. When I see stars, I go nuts inside and fuck harder. Every time it’s afterward that I go numb and feel the guilt, probably like I will when I stop typing and read it back. Now I’m thinking Oh My God, who is this…it sounds bad considering I know what I’m doing, but I am thinking that as far as I can ever tell I’m a pretty good lay!

Yes, I found a travel size tube of KY. No I didn’t tell him because I still would like to avoid anal.

I hear whore and I picture some old witch dressed like Madonna on a street corner. I think slut and I picture Mean Girls in short pleated skirts or some mopey emo girl. Maybe when I’m 50 I’ll be a whore, but let’s assume this will be a distant memory by then.

So I thought about it too, whether they have done this to others. I sort of doubt it. You had to be there when it happened, and you can’t picture every detail like it happened. It’d be a book if I tried to write everything with enough detail to explain it all. It wasn’t like they looked up my dress and said “Presto! Now for the sex!” It was minutes, there were pauses, they hesitated, I definitely hesitated. Details? After we had sex the first time the teacher went and got me paper towels off of his counter to help me clean up. The specialist told me it’d all be okay about a hundred times. I don’t know…I guess I think no…because both of them just seem a little too excited. Maybe the teacher, since he’s always consistent, but the specialist for sure keeps trying little changes, like he’s experimenting for the first time.

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by Anonymous on Oct 7, 2020 at 8:45 AM

With regard to him getting bored, don't count on that happening for a long time. Whether you want to think of yourself that way or not, he considers you on demand head and pussy; no matter how much you dislike the term, you are, in his eyes, his personal whore. His only disappointment so far is not being able to give you a full bore ass fucking. [Best keep that KY handy since I think you'll be carting another load of his cum home in your tight rectum. ] He's not going to lose interest while he can put you on your knees each week and blow his load in your mouth or bend you over his desk to fill your pussy. So unless you become physically unattractive in his eyes [age, weight, accident], he's going to keep fucking his fit side piece for years to come.

Oh, and it's so cute that you think he'd be better served and more excited over a wife or regular girlfriend. Either of those take effort unless he's a complete pig. He has to be concerned with feelings and pregnancy and time of the month with a wife or girlfriend. There is always in the male mind some effort that has to be made to get sex [or more specifically, head to completion with a swallow at the end.]

Does the "seeing stars" with the specialist reflect on his sexual prowess, as in skill level, cock size, aggression level [as in hair pulling, spanking, tit squeezing and the like]? Does your husband regularly make you "see stars"? Does the guilt not only reflect your moral qualms about the situation, but also a sneaking suspicion that you enjoy getting pounded by the specialist a little more than you should? Is part of your physical and mental enjoyment entwined with feeling "forced"? Many women I've chatted with have had a "thing" for not being given a choice in the matter and having massive orgasms because there was a threat over their head. And it didn't have to be physical; a no win situation where the choice was between unwanted sex or something they perceived as worse set fire to their libidos in ways they never thought of before.

You really need to expand your vision with regards to whores. There are plenty in the straights you mention, but there are also Vegas courtesans at the higher appearance and skill level that probably make more per year than most people but still, at their core, understand they are trading access to a very nice body for money. You're just trading yours for a cash equivalent. You're giving them cock access to all of your holes and those very nice sounding tits in exchange for something you value, your son's continued attendance at the non-ghetto school.

You mention the specialist making loads of little changes. That's part and parcel of him keeping things fresh and testing your limits. If it's not too personal [like anything would be after all of this] does your birth control inhibit you having periods? If it does, all well and good. If it doesn't make sure you have the KY handy the next time you visit the specialist while you're bleeding.

One final note, even though you're feeling embarrassed and maybe a little guilty about committing all of this to pixels, your story is gaining some fans as you reveal more details. Right now, your tale of debauchery has 65 "That's Juicy!" ratings.

Oh, and I'll add my personal thanks for being patient with me and my never ending stream of remarks and questions.

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by nunya on Oct 7, 2020 at 10:24 AM

I hate to be the bearer of bad news, but it's going to be a long time before the two of them [particularly the specialist] get bored with having a fit 33 year old side piece who didn't enter into the situation completely voluntarily. The specialist is enjoying himself greatly right now and part of it goes totally against your speculation that he would be better satisfied with a wife or long term girlfriend.

Think about your sex life at home for a second. Does your husband ever come into the bedroom at night with a big smile on his face and the certain knowledge that he can have you any way he wants you by merely telling you what he wants? Can he step into your boudoir and inform you that he expects you to drop to your knees and suck his cock until he cums? Or bend you over the edge of the bed and shove his cock up your ass with spit as lube? If you answer 'No' to either of these hypotheticals, you can understand why the specialist prefers his personal whore to a wife or girlfriend. At home, sex isn't a given - particularly of whatever variety he craves at the moment. It has to be negotiated for with frequent checks for mood, arousal, and desire. With you, he doesn't even have to check for panties. He simply lays you face up or bends you over the desk and takes his pleasure, whether you get any or not is up to you.

By the way, minor point of curiosity, are your pubes shaved? Depending on how much older the teacher is, his wife may well be natural and a bare pubic mound is an exciting novelty for him. Of course, if he and his wife are that old, you likely have the tightest pussy he's been inside of in years, and he's not going to tire of that before the end of the year.

Another fleeting thought and question is whether either or both of them make you line up their cocks to put them in your pussy. I know it's a minor thing in most relationships, but in this situation that small act makes you a collaborator in your own debauchment. It makes you a participant, not a simple vessel waiting to be filled.

And keeping my string of too personal questions going, does your birth control inhibit your periods? If so, it's all good. If it doesn't, keep that KY handy since that may be one of the specialist's triggers for wanting anal.

You speak of "seeing stars" and getting extremely turned on while the specialist fucks you [a little roughly] and then feeling guilt afterwards for having enjoyed yourself. I guess my question about this phenomenon is also two fold. Is the sex itself the trigger? Do you "see stars" when your husband is fucking you? If it's less often or not at all, is the specialist bigger, better, or more aggressive than your husband? Is the big trigger for the guilt the moral situation you find yourself in or the fact that you find yourself enjoying your "forced" sexual encounters more than your marital ones?

Just an observation, you might want to recalibrate your mental image of whores. They aren't all 3rd Avenue junkies with a trail of injection scars and dresses that don't cover their ass while standing on the corner in the middle of winter. There are lots of mid level ones that make a respectable living and some high end ones that do better financially than a lot of executive types. The base idea is the same though. They are trading access to their bodies and orgasms for men for money [or in your case a money equivalent.] There's a reason it's called the world's oldest profession.

Not to inflate your ego too much, but they could have been very excited at the idea of having a sexy thirty something in the harem to replace the forty something that was looking a little haggard these days and getting a bit pudgy. So, there could be others and all of the hesitancy you saw was over whether you would "play ball" and not rat them out for putting the proposition forward. If I were a betting man, I'd guess the teacher is only nailing you. The specialist, on the other hand, may have two or three others on the hook. In fact, one of them having a scheduling conflict may well be the reason you're getting called on twice this week.

A few quick things in closing:

I don't know if you've been paying attention, but your tale is getting popular. It's up to 65 "That's Juicy!" votes. That seems to track hand in hand with original posters coming back to answer questions and add details.

I do appreciate you indulging my curiosity.

And finally, always copy your text before you hit the Submit button. I forgot to this morning and about 700 went "POOF", into the ether. I'm sure this comment doesn't cover everything the other did, but it's as close as I can get.

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by Anonymous on Oct 7, 2020 at 11:04 AM

Going to make this a quick reply…lots of questions twice in a day… So there isn’t really a way for me to slow things down is what you’re saying? If that’s true, then I imagine something has to blow up at some point. I wasn’t thinking that a wife or spouse would arouse him more. My point is there’s a commitment to a long term relationship versus if I want variety I want different. I’m committed to my husband ( I know – until now) versus I was with a decent number of guys before I committed to him. Variety of sizes, colors was part of what made it an adventure. With clothing, I would have thought the adventure would be sexy lingerie and see my have to strip piece by piece, though this is quicker.

I occasionally go shaved, otherwise I have a small patch just above…not quite a landing strip, more of a small V that just goes up about two inches. I got used to being bald, but my husband prefers some hair. Birth control…I’m on depo. There’s random spotting between shots but no full-blown periods. I’m supposed to be able to stay on the shot for another couple of years before I need to switch to daily or something else.

Ok, so I’ll just go with you that there may be others. My situation and my son’s situation are pretty unique, though, so I would think it would be hard for all the stars to align for them to have a harem. I think had I cared about my dress being in my lap when I leaned forward that first time, the proposition never would have happened. I really didn’t put out any signals I wanted something until I got really desperate for my son and even then the dress was unintentional…have you ever sat in an elementary school chair as an adult, especially wearing a short-ish dress?

Ok, don't expect more from me tomorrow...can't imagine what you'd ask next...but I'm sure I will have an update after Friday.

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by Anonymous on Oct 7, 2020 at 2:27 PM

As an active cuckold I am jealous of your husband. But my wife tells me everything and she uses protection. Are they bigger than your husband? Would love to hear about your first time going black.

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by nunya on Oct 9, 2020 at 8:22 AM

I'm looking forward to your update this afternoon. I'll hold off on my usual twenty questions until then, but there are a couple of things I'd like you to reflect on and pay attention to today.

On the notice, pay attention side, if the supervisor puts you on your back on his desk today, see how big he is on eye contact. Does he demand it? Is he constantly looking for your recognition that it's him and not your husband fucking you?

One thing you didn't answer earlier that I'm curious about. If this goes into the next academic year and your son gets a female teacher, would you be accommodating to her if she were interested in weekly head to keep your son in her class at the "good" school?

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by Anonymous on Oct 9, 2020 at 11:45 AM

If this posts twice, it's the site's fault, not me...

Quickly on your one question…sure I’d be with a woman for my son…that I could almost tell my husband and he’d probably just want to know what she looks like and whether he’s invited. Maybe that's something you can ask me later, but way off topic.

So…I think I have a problem, but it’s different than what I thought it would be, or the one I already have. I thought the specialist would be ramping up our meetings so he’d get more sex out of me. To a point that’s sort of what happened, but instead of it being him just wanting more sex, I think he’s crushing on me. Well, in my mind I know he is.

I brought my son to school pretty much on time and in time for meeting the specialist. The front desk eyeballed my outfit and audibly “huffed” and I got a stern look of “you should know better than to dress that way”. Short sweater dress with knee high boots. Yes – no panties, but I had on a bra. She took me back to the specialist’s office. When I got in I said the typical wary “Hello” and he says “Hey” sort of excited like. I put my purse on his desk assuming we’d be leaning over something or straddling something in a minute or two. Instead he says “How about coffee?” I said “Huh?” but I know I was thinking “What the Fuck, No.” He said we can go out for coffee. He even asked if I wanted to ride with him and I said I probably shouldn’t leave mine in the parking lot…he agreed, thank God.

He took me to a very busy part of town, even now during COVID. If I told you, you might even know the area…it’s touristy. He got the coffee and he wants to talk, asking me about my son, even about my husband, about me and where I grew up. I gave short answers but I’m weirded out that he’s asking all this stuff.

After this he says, “Let’s go somewhere we can hang out.” Fortunately he lets me follow him without complaining. He leads me into a condo complex not too far away and I freak out. I yelled out “Oh shit, not fucking way!” in my car really loud. He took me to HIS condo. He got me inside, it’s one level with a big window overlooking the community pool. He starts kissing me, so without too much hesitation I return a full-on tonguing and I guess you’d call it an intimate embrace with his hand running through my hair and rubbing my ass with the other. He tells me how beautiful I am and I thank him. He stops and we kiss again the same way, then he lifts up my dress so he can fondle my ass. We helped each other pull off clothing …a little in a rush but not really. He laid me down in HIS BED, and got on me missionary. He didn’t just force his way in, he kissed me first, kissed up and down my body a little, stayed on my chest to suck each nipple hard, ate me out a little to lube me up. He finally penetrated me and buried himself as deep as he could and laid like that kissing me again. He took forever, I’m not sure how long in minutes but it’s a long time. Yes, it was very good sex, very warm, hit all the right places. He had me orgasming twice before he got to his finish and we orgasmed together.

After that I’m thinking I got to get out of here. But, he rolled onto his back and pulls me against him, laying my head on his shoulder. He puts an arm around me and runs fingers along my side. We laid for a long time. Then he turns and starts kissing me again. He guides my hand to his shaft and helps me pump him for a few strokes. Then he guides me to cowgirl him. I love cowgirl and we had not done this yet. The sex felt excellent. Eventually he came in me again and we laid a while with me on top of him kissing. Of course there’s no clock by the bed, so I start to worry about the time. I finally tell him I have to go. He says “When can I see you again.” And I quickly reply “Wednesday” – I wanted to shout it at him. As I’m getting dressed he sort of pouts and says “Can I see you earlier?” and I reply more firmly, ”Please, Wednesday, now I really have to go.” He replies “Ok, Wednesday usual time.” and kisses me on my way out of the condo.

Between drive time, coffee and bedroom time, we were together almost four hours from the time I got to his office at school. But I am freaking out. He took me to his condo – his fucking home! He didn’t just screw me…I know the difference, that was intimate to him.

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by nunya on Oct 11, 2020 at 11:42 AM

Damn. The difficulty factor of your situation has jumped at least threefold.

If all is as you say, he's developed a serious infatuation for you that goes well beyond the defined boundaries of your agreement. The fear now has to be how this will affect relationships all around. I fear he may develop "ownership" issues over the use of your body. I wish I had been around to respond Friday evening or yesterday. I would have asked you to keep an eye out for any changes in behavior by your Saturday fuck buddy. If he's starting to have the urge to control you, it might manifest first by him talking to the teacher about limiting his contact.

He has discovered that he likes having the ability to, if not order, at least influence how you act when you are not around him [you asking permission to put on panties when you leave]. Showing an interest in you beyond getting his weekly piece of ass and blow job - the chit chat, coffee, and questions about your son and husband sound a lot like a man in search of an opening for an affair.

I assume from your description of the situation that he rarely display any sort of tenderness towards you and your past visits to his office have more closely resembled a midday visit from a whore - a quick BJ, some pussy eating to get his motor running again, and a hard fuck with lots of groping but no kissing. This visit sounds 180 off from that. The outline you give for this visit is more a relaxed nooner with a wife or girlfriend.

Aside from your base sexiness and technical skill in the sack, I don't get the impression you did anything to encourage his sudden obsession. This is all on him and his imagination. He has read your skill as enthusiasm and your orgasms as affection. I get the feeling he's had an entirely unsatisfying sex and romantic life and having you alone in his office, willing to do whatever he commands has been the highlight of his sex life.

I don't know how to do this gently, but you'll have to get the idea across to him - firmly - that you are there to service him and you don't have any emotional investment in the sex even though you may swallow his cum and orgasm from his skilled fucking. You may have to allow that you like him on a personal level, but the sex is whore [even if you don't like the word] level and doesn't carry any emotional weight, not matter how good it feels on a given day.

That is going to be something to ponder. The obvious pitfall is how to do it without putting him on a path toward retaliation - whether to you, your son, or your marriage.

One off the wall question that came to me while writing this has to do with you giving him blow jobs. You've mentioned one occasion where you had cum leak out on the back of your dress when you went to lunch with a friend right after one of your meetings. Same situation, but how do you get rid of the cock breath that goes with taking a big load in your mouth? Second part of the question; have you ever been to some public function after one of these meetings and realized you had cum stains on your shirt or dress front?

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by Anonymous on Oct 12, 2020 at 6:15 AM

Anyone else having trouble posting to this series?

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by Anonymous on Oct 12, 2020 at 9:25 AM

Damn. The difficulty factor of your situation has jumped at least threefold.

If all is as you say, he's developed a serious infatuation for you that goes well beyond the defined boundaries of your agreement. The fear now has to be how this will affect relationships all around. I fear he may develop "ownership" issues over the use of your body. I wish I had been around to respond Friday evening or yesterday. I would have asked you to keep an eye out for any changes in behavior by your Saturday fuck buddy. If he's starting to have the urge to control you, it might manifest first by him talking to the teacher about limiting his contact.

He has discovered that he likes having the ability to, if not order, at least influence how you act when you are not around him [you asking permission to put on panties when you leave]. Showing an interest in you beyond getting his weekly piece of ass and blow job - the chit chat, coffee, and questions about your son and husband sound a lot like a man in search of an opening for an affair.

I assume from your description of the situation that he rarely display any sort of tenderness towards you and your past visits to his office have more closely resembled a midday visit from a whore - a quick BJ, some pussy eating to get his motor running again, and a hard fuck with lots of groping but no kissing. This visit sounds 180 off from that. The outline you give for this visit is more a relaxed nooner with a wife or girlfriend.

Aside from your base sexiness and technical skill in the sack, I don't get the impression you did anything to encourage his sudden obsession. This is all on him and his imagination. He has read your skill as enthusiasm and your orgasms as affection. I get the feeling he's had an entirely unsatisfying sex and romantic life and having you alone in his office, willing to do whatever he commands has been the highlight of his sex life.

I don't know how to do this gently, but you'll have to get the idea across to him - firmly - that you are there to service him and you don't have any emotional investment in the sex even though you may swallow his cum and orgasm from his skilled fucking. You may have to allow that you like him on a personal level, but the sex is whore [even if you don't like the word] level and doesn't carry any emotional weight, not matter how good it feels on a given day.

That is going to be something to ponder. The obvious pitfall is how to do it without putting him on a path toward retaliation - whether to you, your son, or your marriage.

One off the wall question that came to me while writing this has to do with you giving him blow jobs. You've mentioned one occasion where you had cum leak out on the back of your dress when you went to lunch with a friend right after one of your meetings. Same situation, but how do you get rid of the cock breath that goes with taking a big load in your mouth? Second part of the question; have you ever been to some public function after one of these meetings and realized you had cum stains on your shirt or dress front?

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by nunya on Oct 12, 2020 at 9:44 AM

Rather than wait for another day for the long posts I've submitted to be approved, let's see if I can sneak things through three or four sentences at a time:

Damn. The difficulty factor of your situation has jumped at least threefold.

If all is as you say, he's developed a serious infatuation for you that goes well beyond the defined boundaries of your agreement. The fear now has to be how this will affect relationships all around. I fear he may develop "ownership" issues over the use of your body. I wish I had been around to respond Friday evening or yesterday. I would have asked you to keep an eye out for any changes in behavior by your Saturday fuck buddy. If he's starting to have the urge to control you, it might manifest first by him talking to the teacher about limiting his contact.

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by nunya on Oct 12, 2020 at 9:45 AM

2 of 4?

He has discovered that he likes having the ability to, if not order, at least influence how you act when you are not around him [you asking permission to put on panties when you leave]. Showing an interest in you beyond getting his weekly piece of ass and blow job - the chit chat, coffee, and questions about your son and husband sound a lot like a man in search of an opening for an affair.

I assume from your description of the situation that he rarely display any sort of tenderness towards you and your past visits to his office have more closely resembled a midday visit from a whore - a quick BJ, some pussy eating to get his motor running again, and a hard fuck with lots of groping but no kissing. This visit sounds 180 off from that. The outline you give for this visit is more a relaxed nooner with a wife or girlfriend.

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by nunya on Oct 12, 2020 at 9:46 AM

3 of 4?

Aside from your base sexiness and technical skill in the sack, I don't get the impression you did anything to encourage his sudden obsession. This is all on him and his imagination. He has read your skill as enthusiasm and your orgasms as affection. I get the feeling he's had an entirely unsatisfying sex and romantic life and having you alone in his office, willing to do whatever he commands has been the highlight of his sex life.

I don't know how to do this gently, but you'll have to get the idea across to him - firmly - that you are there to service him and you don't have any emotional investment in the sex even though you may swallow his cum and orgasm from his skilled fucking. You may have to allow that you like him on a personal level, but the sex is whore [even if you don't like the word] level and doesn't carry any emotional weight, not matter how good it feels on a given day.

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by nunya on Oct 12, 2020 at 9:46 AM

4 of 4

That is going to be something to ponder. The obvious pitfall is how to do it without putting him on a path toward retaliation - whether to you, your son, or your marriage.

One off the wall question that came to me while writing this has to do with you giving him blow jobs. You've mentioned one occasion where you had cum leak out on the back of your dress when you went to lunch with a friend right after one of your meetings. Same situation, but how do you get rid of the cock breath that goes with taking a big load in your mouth? Second part of the question; have you ever been to some public function after one of these meetings and realized you had cum stains on your shirt or dress front?

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by nunya on Oct 12, 2020 at 9:54 AM

Nope. I didn't mis-number. There is a part three floating in the ether that won't post.

OP, if you want the full message in order, drop me an email at nunya001122 at g m a i l d o t c o m I'm tired of dealing with this.

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by Anonymous on Oct 12, 2020 at 11:43 AM

There isn’t a lot to comment on since this weekend and Friday. Right now I am dreading Wednesday and see what I walk into with the Specialist.

The ONLY thing unusual about my visit with the teacher on Saturday is that while I was riding him, he opened the zipper of my sports bra so he could see my breasts and feel them. Usually he’s holding my hips or has to use his arms to leverage himself on the seat. I’ve thought about it a few times and I think maybe it was the first time I had on a front zip top.

The specialist was never like this before. No kissing on the lips or face before. Yes, the “where do we go from here?” question is killing me.

For your other question…I always chew gum, it’s probably part of what makes people think I’m more vacuous than I really am…and I keep something to drink in the car for after my meeting with him. Yes I leaked but so far it was just when I went to meet a friend and she told me I had a stain on my dress…I’m sure she knew what it was from considering where is was on my ass, but she didn’t say anything.

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by Anonymous on Oct 12, 2020 at 6:42 PM

I logged in and replied but hasn't shown up. I'll check back after the next part of the nightmare (Wednesday) and see if I can post.

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by nunya on Oct 13, 2020 at 8:50 PM

Aside from your base sexiness and technical skill in the sack, I don't get the impression you did anything to encourage his sudden obsession. This is all on him and his imagination. He has read your skill as enthusiasm and your orgasms as affection. I get the feeling he's had an entirely unsatisfying sex and romantic life and having you alone in his office, willing to do whatever he commands has been the highlight of his sex life.

I don't know how to do this gently, but you'll have to get the idea across to him - firmly - that you are there to service him and you don't have any emotional investment in the sex even though you may swallow his cum and orgasm from his skilled fucking. You may have to allow that you like him on a personal level, but the sex is whore [even if you don't like the word] level and doesn't carry any emotional weight, not matter how good it feels on a given day.

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by nunya on Oct 13, 2020 at 8:54 PM

I tried part 3 of my weekend reply four times and none posted. It looks like it's only allowing the shortest of replies, written in real time, to post.

No idea what is going on. You may have to write another confession from scratch if your desire is to keep everyone in the loop. Or you can email me direct.

I wish you well on your Wednesday appointment.

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by Anonymous on Oct 14, 2020 at 10:41 AM

Not sure if my last post will ever show up, so since my “intimate” afternoon with the specialist, I did meet with the teacher on Saturday. The only unusual thing about that was that this was the first time he had me expose my breasts while we had sex in the car. It was the first time I wore a sports bra with front zip, so maybe he just took advantage of that.

Today’s meeting with the specialist has me really confused now and I am trying to figure out how to handle it. Early in the morning, he texted me and said “dress super sexy.” I took that to mean short skirt and something tight. So I wore a dark red leather mini skirt and tight black sweater. I had a light jacket on but I still got a dirty look at the front dress again.

Back in his office, the specialist closed the door and says how much he misses me and couldn’t start thinking about me. He kissed me on the lips again and we kissed for a minute or so. He started rubbing over my ass and says “I have to have it!” I thought at first he wanted to go directly to anal, but instead he tugged my skirt up so the hem was halfway up my butt but not all the way up. He turned me over and took me from behind. It was such a good feeling I just went with it. The skirt was compressing my ass and keeping everything tight. He was tight inside me and it all felt very good. He didn’t last long at all and came hard into me.

As he finished I went to stand up, but he held me down and pulled my skirt ht he rest of the way up, fully exposing my ass. I looked down at the floor and heard him opening a plastic lid on a container. He stuck a cold wad of lube over my asshole and began rubbing it around. This was it, we were doing anal today. He lubed me all the way up and just said “Ok, you can play with yourself if it helps.” He wasn’t fully hard at first, but he stuck his penis in my ass crack and rubbed it around, then he slowly began feeding it into my ass. It has been a little while since I did anal, especially with someone like him and really awkward considering he’s just using me how he wants. I was tense at first, so he slapped my ass cheek hard a couple of times and said I should try to relax.

Once he firmly inserted the head of his penis in me, I used one hand to start fingering myself, slowly at first, then harder as his shaft began to slide in. It was sort of an odd angle and I had to bend my knees to get the angle right, but he started pressing his way deeper and deeper. I finally asked him to not go in so far and he laughed a little and said “We’re going all the way, just try to relax.” The farther he went in the more I rubbed myself until I had a thumb on my clit and two fingers working my pussy. I came by myself which made me tighten my ass. He began pumping faster after that and went in so deep I felt like I wanted to choke. He didn’t last long once he picked up speed and I felt him come again in my ass.

After that, I almost expected us to talk for a bit, sort of like we did at his condo. Instead he said “That felt great, you are awesome.” and started getting dressed. I pulled down my skirt and just stood there with my butt a slimy under my skirt. He finally said “Ok, let’s meet on Monday next week.” I said I thought we were meeting Wednesdays and he said, “No, next week Monday, or you can text me and we’ll meet Tuesday instead.”

So this time it was just about sex, but he finally had me do anal. I don’t know if he’ll be affectionate, or cold, I don’t know if Monday will be it or if he’ll say next Friday too. It’s so hard to figure out how to feel about all of this…scared he’ll escalate again…relieved that it was just sex today…I don’t know.

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by Anonymous on Oct 14, 2020 at 1:35 PM

Before I go too far into your last email, I want to share something you may find objectionable, but that might color my analysis so I want it out front. I'm highly envious of the specialist. Being an unrepentant horndog of long standing, I find the position he's in - having control of a sexy early thirties woman who can't, or at least hasn't, said no to any of my sexual demands - more than a little desirable.

Now on to why you come back to read.

He's sending highly mixed signals right now and I suspect it's on purpose. Demanding you dress sexy is the start. Have you told him about the suspicious looks and raised eyebrows the receptionist has been giving you, even on days you're not under orders to slut up your look? As a point of simple curiosity, did you have your regulation sports bra on under the sweater? If not, were your C cups mobile enough to let her know you were unsupported?

The kissing and murmurings about not being able to quit thinking about you were a continuation of last week and an approval of sorts of your outfit. The approval was not simply because he liked the look, but because you had obeyed him. You didn't dwell on your response to his kisses and sweet nothings, but if I had to guess, I'd say you were somewhat neutral. You didn't object to him kissing and manhandling you, but neither did you cup his crotch with your hand or explore his mouth with your tongue like you were checking for loose fillings.

And at that point, a switch was flipped and he may or may not have made a conscious decision to push the envelope on your compliance since he wasn't getting the returned physical intimacy he hoped for in response to his kisses, or hearing how you had thought of him all weekend or how much you were looking forward to getting ravaged by him today.

I'm surprised he didn't demand oral to start things off, but perhaps he thought he might lose that initial load in your mouth and he was already plotting where he wanted to leave his loads today.

Again, for the sake of my own purient interest, when he initially bent you over his desk, were you already wet enough to fuck without discomfort? Did you orgasm during that initial screwing while he was cumming hard in you?

To be blunt, given where things went next, I'm amazed he didn't tell you to give him oral between fucks. Firstly to get him hard again, but secondly [and almost as important] to demonstrate his control over you - making you humble yourself on your knees while you cleaned your combined juices off of his cock. After the fumbling around he did to get hard the second time, don't be surprised if that's on the menu the next time he wants anal.

Now for the main event, the anal. He didn't ask, he didn't suggest, in your telling of the tale, he simply did it without consideration of whether you wanted or accepted having your ass opened up with his cock. This was a major display of dominance; particularly the part where he said you were going to take all of him, even if it was uncomfortable for you - his pleasure in that moment was paramount. In his thinking he was being kind enough when he gave you "permission" to masturbate while he fucked your ass for what will likely be the first of many times to come.

Did him taking you that way drive home the notion that you're his slut, his whore, to do with as he will?

A few more things before I close this time....

Did you drip copious amounts since he loaded you up front and back? What shape was the dress in when you got home? What about your ass? Sore? Leaking? Was there a snail trail down the inside of your thighs?

Do you have to check out of the school as well as in? Has the receptionist seen you in your guilty faced, just fucked mode as you exited?

And again thinking of her, how thick and soundproof is the door to the specialist's office? More to the point, how loud of a fuck are you? Do you think she might hear if she hangs around his office while your inside servicing the specialist?

(13) (0)

by nunya on Oct 14, 2020 at 1:38 PM

I'm glad it posted, but I have no clue why the system logged me out and posted it as Anonymous.

(0) (0)

by nunya on Oct 14, 2020 at 1:46 PM

Oh, one last thing with regards to the schedule.

If you show up Monday or Tuesday, expect to do a command performance on Friday. He may well take you back to his condo again so he can give your ass a nice leisurely fuck doggie style.

Or if he's gone totally into dominance and is unhappy you're not completely smitten with him, he may suggest tying you down and blindfolding you so he can sneak invite some friends over to sample your holes.

(0) (0)

by nunya on Oct 14, 2020 at 2:55 PM

One last "devil in the details" question. Your description of the specialist was that he pretty straight forward - lube you up and stick it in. Was that the case? Did he not finger you or give you any sort of preparation other than putting a dollop of lube on your asshole?

And so about how thick is the specialist's cock? Quarter? Fifty cent piece? Two fingers side by side?

(7) (0)

by Anonymous on Oct 14, 2020 at 6:47 PM

Your first thought made me laugh a little. I know it’s about the smutty stuff. Like I said, I got turned on and do get turned on by the sex. The weird or funny thing is the more I think about my Friday meeting with the specialist, the more I want it to just be about sex and to just be used and pleasured and I guess be promiscuous.

Okay, so thinking about it all…I think I’m scared he does have feelings for me. It’s that whole “kissing on the lips” thing that I’ve always heard about that so long as you aren’t kissing it’s nothing more than sex. Not love, not emotional. I’m almost relying on it just a series of hookups and then I can go away and tell myself it’s just my way of helping my son…yay, now I’m a hooker on top of it all and my payday is help for my son…In the moment I can just get dirty and physical. It’s been close to ten years since I did anal, and it was uncomfortable just like I thought it would be. But, pleasuring myself while he was in my ass made my puss extremely wet.

When we had sex (the specialist)…there’s a little bit of touching and foreplay, but today he was more forceful so when he pushed in, he literally pushed in. Yes I am fairly wet when I get to the office for our meetings, mostly anticipating what we’ll do. I get stimulated pretty easily, always have regardless of partners, and that shocks me a little that someone taking advantage of me has turned me on. And yes, I orgasmed during sex today. Today he spit on his erection to lube up for the sex, but it wasn’t a gentle massage for foreplay, it was pretty much wham and he was in.

It does scare me a little that he doesn’t seem to have limits. Yes, he literally took my ass today. He took little pauses to adjust or to respond if I wiggled or flinched, but he didn’t go easy on me just because I’d be in pain for a minute. He’d slow, maybe adjust position slightly and go right back to it. Giving him oral after sex is okay to me, though a lot of times so far he just transitions form one to the next. I think…not sure how this works…that he gets hard playing with my holes as much as he would if I sucked him back to life.

I was pretty much a mess after the meeting, cum-wise. Yes, I was leaking out of both holes, my pussy was throbbing from me fingering myself so hard, and my ass cheeks were slippery form the lube. I did stop at a couple of shops and got coffee before going home, so I’d be lying if I didn’t admit that it feels wild to be ordering coffee while I feel drips of jism leak out my puss. When I get home and think about it I have regret and guilt, but driving around right after it I feel…kinky?

Fortunately the front desk doesn’t require check-out, so I bypass that B**** as much as I can. The specialist’s office is toward a corner of the building, no windows and it’s cement block walls. It’s actually the ideal place to do this.

I read a few stories on cosmo today about girls cheating on their boyfriends and husbands and I thought to myself “ I’m doing this.” I’m so scared of being caught, but I look forward to it more. I’m even starting to wish the teacher would get more creative, but I don’t want to introduce him to it so that he doesn’t get too many ideas, either. Get it over with on one hand, enjoy the raw sex in the meantime if I have to…if that makes any sense. The specialist has something going on in his head, so that’s weirding me out. But I guess look at me…same reason I keep coming back here now…I’m into it and I’m convincing myself I can manage it.

(24) (0)

by Anonymous on Oct 17, 2020 at 8:32 AM

Just admit you like being used and submit to what you are. You'll enjoy it more and probably less likely to break down in front of your husband. If they don't help your kid you can bail but you'll probably need some side action now. Live it up while you're young!

(1) (0)

by Anonymous on Oct 17, 2020 at 9:54 AM

Did you get out of the car to get coffee and when you visited the shops? Given that it was a short leather skirt, do you think the cum dripping down your inner thighs might have been visible? Does the idea that someone may have noticed the cum by sight or scent make you wet?

What sorts of things have you imagined introducing the specialist to that you've rejected so as not to give him the idea that you're more into getting used than you let on? Have you used any of them in verbal play with him during sex?

Going back and glancing through your original post, it finally dawned on me that your son is only six. That typically puts him in first grade. Depending on how your school system is structured, you might have to be the specialist's sex toy for the next five to six years. Do you think you can tolerate the situation with the knowing looks from the bitch at reception once or twice a week? What about if the specialist gets tired of one on one debauchery and wants to include a friend or two in those Friday romps at his condo after he figures out you're a nice piece of ass and not an affair?

What if he gets truly freaky and starts demanding bondage or piss play to thoroughly debase you? You said he seems to have no limits. What is the furthest out demand you can imagine him making of you?

(1) (0)

by nunya on Oct 19, 2020 at 8:27 AM

Tried twice to post an additional, longer note, both with and without logging in. I'll give it a couple of hours in case it needs someone's approval, but if it doesn't show I'll try pasting my cached version again.

(0) (0)

by Anonymous on Oct 19, 2020 at 9:48 AM

For the record and get a jump on your questions…I am sitting with a lot of cum in my puss and will be taking a long shower shortly. It is leaking and I feel it running out onto the chair but I can wipe it up when I stand up.

I’m trying to be more confident about everything after last week. I’m getting what I need for my son, I’m not harmed by the sex…maybe a little confused and used, but I feel good…and I’m handling my life at home without too much drama and my husband and son seem happy.

Saturday morning I got a text from the teacher that he couldn’t meet me. The rest of the day I felt relaxed and calm, almost like I was free or didn’t have a cloud over me. I just went about my business. No texts on Sunday from anyone, so no excuses about having to go shop during football and no sneaking around.

Monday morning, I drove into the school to meet with the specialist. I purposely dressed up for today, hoping maybe I’d catch him in a mood where he’d go fast and I could get out of there. Didn’t happen. But, I tried. I wore a tight white gold skirt that just barely covers my rear and shows off almost my entire thighs. I put on a long sleeve exercise shirt and left the zipper open to show off my cleavage. No bra, no underwear of any kind, no shorts under the skirt…just some white sneakers. I wore a jacket to check in, got the obligatory look over by the front desk, and got back to the specialist’s office.

The teacher was in the room with the specialist. I was very surprised and didn’t say anything at first. The specialist helped me off with my coat as the teacher said “Sorry I couldn’t make it Saturday.”

Both of them came in me twice today, three times in the puss and once in my ass. The specialist started from behind with me leaning over to give the teacher a blow job. They didn’t undress me. Twice I could feel the teacher getting close and both times he backed down or slowed me down so he wouldn’t come. The specialist kept a smooth rhythm from behind rubbing my asshole with his thumb and eventually he pulled me close and came. As soon as he pulled out the teacher walked away from my face and went behind me. Just a few deep thrusts and he buried himself in me too.

“Your tits look amazing in that shirt” the teacher goes. He usually just grabs on to hold them during sex, but now he came up and caressed them under my shirt. Then he helped me pull it off and for the first time he began to suck on my breast. He sucked hard, more as if he was breastfeeding than anything. The specialist stood behind me with a hand on my hip and the other rubbing my ass through my skirt. This went on for several minutes, the teacher switched to my other breast. The specialist came around and still rubbed my as with one hand but took the other to pull my head in and we began kissing while the teacher still sucked on me. The teacher thumbed my clit too then would run his thumb into my puss a few times to make me jump or tense a little, then he’d play some more with my clit while he continued to suck.

Then the teacher guided me to get on the floor. With me laying on my back, my skirt rolled up around my waist by itself. He didn’t hesitate and mounted me. He wasn’t completely hard, at least I don’t think so, but hard enough that he could push into me and slowly fuck me. The specialist just watched us slowly pumping himself back to life. The teacher went for a while, just sex, no kissing, looking at me or down at my breasts. He got a little harder, stiffened, and came in me again, not nearly as big as the last time but I could still feel it come out. The specialist stood over top of me as the teacher rolled off, and he started lubing his penis. He got down on his knees in front of me and lifted my legs way up and out. “Here, hold on” he told me to hold my legs apart. I said I didn’t think I could do it this way and he said “Just hold them, I’ll go slow.” He entered me in the ass very slowly and each time went in just a bit deeper. From this angle I felt so full, like I was being stuffed. This was the first time I did anal on my back. I felt dizzy as he pushed deeper. I relaxed more until I felt him in enough that his balls touched my ass cheeks. He pumped gently after that, moving in my ass and I felt completely full. He began using his hands to help hold my legs. I couldn’t help it and I knew it would show I was into it, but I used my one hand to play with myself so I’d orgasm. The orgasms were amazing, I wanted to clench but his penis was in so deep I ended up relaxing as much as anything, just feeling everything go up my body. I finally said, “please come in me.” He did…I played with myself and we came together.

After all of this we got dressed…well, I pulled my skirt down and put my shirt back on with the teacher’s help. “Are we meeting like this now?” I asked. The teacher said “No, I can’t get out of class like this all the time. We wanted to try something new.” He smiled and the specialist laughed a little. “See you next week.” he said.

I drove home from there. When I got home I looked. I had a big mess on my seat from everything draining. I could wipe it off the leather, but it soaked into the little holes in the leather so I had to wipe it several times.

The sex this time was amazing. I wanted it and I got it. But now I’m sitting at home and I’m feeling nervous. If we keep doing more each time, eventually something will happen. We’ll get caught sooner or later. That time together took a full hour…what if the next time they try it and it talks too long. Nothing new since last time, I still don’t know where this is going.

(27) (0)

by Anonymous on Oct 21, 2020 at 9:08 AM

Hello Less than Perfect Mom,

This is try #9. The other eight have not posted. With my luck, all of them will show up at once. If they do, you have my apologies,

I see you already answered a bunch of my questions but made other remarks to make up for it, so I'll paste what I started with and make some edits as it goes along.

I have a question about the logistics of your weekend romps in the Home Depot parking lot. What position do you two normally get in? Missionary with him on top? You on top? Sitting, with you riding his cock? Doggie?

You went and serviced two instead of one in the office even though you know that giving in to the specialist's scheduling demands now most likely means he'll want to fuck you again later this week. Were you hoping for the dispassionate, "treat her like a whore" attitude on his part instead of the hugging, kissing, clinging "act like it's an affair" version? Or are you not certain yourself at this point? Jumping ahead a little, I see where the specialist said he would see you next week. Do you think that schedule will hold? Or do you suspect, as I do, that it was a bit of window dressing for his teacher friend and you'll soon get a call from the school informing you of a second, possibly off campus, meeting with the specialist? Or perhaps a direct text from him demanding your presence and sexual compliance somewhere on Thursday or Friday?

This next bit that occurred to me is either a suggestion, or something you've already done and not revealed. When he started asking personal questions during your "coffee date" last week, did you ask any back? Is he married but hiding it? In a serious relationship short of marriage? Single, mostly sexless outside of you and not happy about it?

I go there because the thought occurred to me [somewhat late] that the reason he went into the affectionate mode is that you're his primary sexual release aside from porn and his right hand. It's said that one of the stark differences between men and women is that men can have sex without emotion but women can't. If you look back at history, I suspect you'll find that doesn't hold up, especially if the guy is getting very little pussy and the woman is getting all the dick she wants or can handle.

There's been more than one man ended up married to his "slump buster" - the woman that ends his sex drought. On the same vibe, many a wife got into the relationship because she was "dickmatized". From what I'm told, it doesn't even have to be an exceptional cock, it simply has to be available and used skillfully enough to give the lass regular orgasms.

Going back to yesterday's session, you took on both of them, gave the teacher some head, had several orgasms of your own, and ended up with four loads in you, I'd say it was a highly successful meeting. Pity the teacher can't get away more often so they both can use you together.

I like that you revealed that you wanted to get fucked. It seems like you're finally investing in the experience, at least on a physical level. I wonder if seeing you get ass fucked, and feeling your mouth on his cock will give the teacher any ideas about expanding the weekend menu in the back of your car. Maybe he'll make going for two orgasms part of the program. Or cumming in your other holes. Given that you say about his erection during the second effort, he might content himself by getting blown while he plays with your tits for his second cum.

I note with no small amusement that the specialist got lost in the moment and commenced kissing you right after you gave the teacher head. It's a small thing in the grand scheme, but a lot of men won't kiss their partner after getting head from them - even if it isn't to completion. Very few will kiss a woman after watching her give another man's cock a tongue bath. Did he continue to kiss you while he was fucking your ass?

Did it make you feel over the top slutty to ask the specialist to cum up your ass while you had the teacher as an attentive audience for your orgasm and debasement?

In the aftermath, did you skirt have any distinct patterns from being rolled up under you on the floor while you were being debauched? Were there any obvious wet stains on it that were so low your jacket wouldn't cover them? Was the receptionist at her post? Is there any chance she or the principal, vice principal, etc. saw you leave?

With three loads, could you feel the cum oozing down your inner thighs and leaving a shiny trail for all to see? If I read your storyline correctly, you cleaned your car seat before you showered and changed clothes. Did any neighbors get a chance to see the disheveled, leaking, "just fucked" you out there scrubbing on your car seat with a semen stain spreading across your skirt?

(0) (0)

by nunya on Oct 21, 2020 at 9:33 AM

1 of 8

Tenth try. I'm breaking it up.

I see you already answered a bunch of my questions but made other remarks to make up for it, so I'll paste what I started with and make some edits as it goes along.

I have a question about the logistics of your weekend romps in the Home Depot parking lot. What position do you two normally get in? Missionary with him on top? You on top? Sitting, with you riding his cock? Doggie?

(0) (0)

by nunya on Oct 21, 2020 at 9:34 AM

2 of 8

You went and serviced two instead of one in the office even though you know that giving in to the specialist's scheduling demands now most likely means he'll want to fuck you again later this week. Were you hoping for the dispassionate, "treat her like a whore" attitude on his part instead of the hugging, kissing, clinging "act like it's an affair" version? Or are you not certain yourself at this point? Jumping ahead a little, I see where the specialist said he would see you next week. Do you think that schedule will hold? Or do you suspect, as I do, that it was a bit of window dressing for his teacher friend and you'll soon get a call from the school informing you of a second, possibly off campus, meeting with the specialist? Or perhaps a direct text from him demanding your presence and sexual compliance somewhere on Thursday or Friday?

(1) (0)

by nunya on Oct 21, 2020 at 9:35 AM

3 of 8

This next bit that occurred to me is either a suggestion, or something you've already done and not revealed. When he started asking personal questions during your "coffee date" last week, did you ask any back? Is he married but hiding it? In a serious relationship short of marriage? Single, mostly sexless outside of you and not happy about it?

I go there because the thought occurred to me [somewhat late] that the reason he went into the affectionate mode is that you're his primary sexual release aside from porn and his right hand. It's said that one of the stark differences between men and women is that men can have sex without emotion but women can't. If you look back at history, I suspect you'll find that doesn't hold up, especially if the guy is getting very little pussy and the woman is getting all the dick she wants or can handle.

(0) (0)

by nunya on Oct 21, 2020 at 9:36 AM

4 of 8

There's been more than one man ended up married to his "slump buster" - the woman that ends his sex drought. On the same vibe, many a wife got into the relationship because she was "dickmatized". From what I'm told, it doesn't even have to be an exceptional cock, it simply has to be available and used skillfully enough to give the lass regular orgasms.

Going back to yesterday's session, you took on both of them, gave the teacher some head, had several orgasms of your own, and ended up with four loads in you, I'd say it was a highly successful meeting. Pity the teacher can't get away more often so they both can use you together.

(0) (0)

by nunya on Oct 21, 2020 at 9:40 AM

OK, it quit taking any comments at 3 of 8.

If it doesn't dump all of my earlier attempts at once and you want to see the rest, email me at

nunya001122 at g m a i l d o t c o m

(0) (0)

by Anonymous on Oct 21, 2020 at 3:13 PM

I'm reading all this and I wondering what is wrong with your son to need all this help at this age?

I bet the people in the front office at school know what's going on whether it's only you or if he's building his harem. You wear a jacket but your legs have to be bare, and when you didn't wear jackets you had on short dresses. You go for meetings every week. I bet you ask the front desk how many parents meet with the specialist as often and she'll either give you a disgusted look or say something to let you know what she thinks.

And you say your husband thinks your son is dumb. What kind of guy is he - rich jerk, introvert, clueless? You imply your life is good but is it for the money?

(0) (0)

by Anonymous on Oct 22, 2020 at 5:35 AM

Hello Less than Perfect Mom,

Hope springs eternal. Let's see if it get through this time.

Before I get to the copy & paste part, have you heard anything from the school or specialist about the urgent meeting you're having come Friday? The one he wants you to dress like a 10th Avenue whore for?

I see you already answered a bunch of my questions but made other remarks to make up for it, so I'll paste what I started with and make some edits as it goes along.

I have a question about the logistics of your weekend romps in the Home Depot parking lot. What position do you two normally get in? Missionary with him on top? You on top? Sitting, with you riding his cock? Doggie?

You went and serviced two instead of one in the office even though you know that giving in to the specialist's scheduling demands now most likely means he'll want to fuck you again later this week. Were you hoping for the dispassionate, "treat her like a whore" attitude on his part instead of the hugging, kissing, clinging "act like it's an affair" version? Or are you not certain yourself at this point? Jumping ahead a little, I see where the specialist said he would see you next week. Do you think that schedule will hold? Or do you suspect, as I do, that it was a bit of window dressing for his teacher friend and you'll soon get a call from the school informing you of a second, possibly off campus, meeting with the specialist? Or perhaps a direct text from him demanding your presence and sexual compliance somewhere on Thursday or Friday?

This next bit that occurred to me is either a suggestion, or something you've already done and not revealed. When he started asking personal questions during your "coffee date" last week, did you ask any back? Is he married but hiding it? In a serious relationship short of marriage? Single, mostly sexless outside of you and not happy about it?

I go there because the thought occurred to me [somewhat late] that the reason he went into the affectionate mode is that you're his primary sexual release aside from porn and his right hand. It's said that one of the stark differences between men and women is that men can have sex without emotion but women can't. If you look back at history, I suspect you'll find that doesn't hold up, especially if the guy is getting very little pussy and the woman is getting all the dick she wants or can handle.

There's been more than one man ended up married to his "slump buster" - the woman that ends his sex drought. On the same vibe, many a wife got into the relationship because she was "dickmatized". From what I'm told, it doesn't even have to be an exceptional cock, it simply has to be available and used skillfully enough to give the lass regular orgasms.

Going back to yesterday's session, you took on both of them, gave the teacher some head, had several orgasms of your own, and ended up with four loads in you, I'd say it was a highly successful meeting. Pity the teacher can't get away more often so they both can use you together.

I like that you revealed that you wanted to get fucked. It seems like you're finally investing in the experience, at least on a physical level. I wonder if seeing you get ass fucked, and feeling your mouth on his cock will give the teacher any ideas about expanding the weekend menu in the back of your car. Maybe he'll make going for two orgasms part of the program. Or cumming in your other holes. Given that you say about his erection during the second effort, he might content himself by getting blown while he plays with your tits for his second cum.

I note with no small amusement that the specialist got lost in the moment and commenced kissing you right after you gave the teacher head. It's a small thing in the grand scheme, but a lot of men won't kiss their partner after getting head from them - even if it isn't to completion. Very few will kiss a woman after watching her give another man's cock a tongue bath. Did he continue to kiss you while he was fucking your ass?

Did it make you feel over the top slutty to ask the specialist to cum up your ass while you had the teacher as an attentive audience for your orgasm and debasement?

In the aftermath, did you skirt have any distinct patterns from being rolled up under you on the floor while you were being debauched? Were there any obvious wet stains on it that were so low your jacket wouldn't cover them? Was the receptionist at her post? Is there any chance she or the principal, vice principal, etc. saw you leave?

With three loads, could you feel the cum oozing down your inner thighs and leaving a shiny trail for all to see? If I read your storyline correctly, you cleaned your car seat before you showered and changed clothes. Did any neighbors get a chance to see the disheveled, leaking, "just fucked" you out there scrubbing on your car seat with a semen stain spreading across your skirt?

(0) (0)

by Anonymous on Oct 22, 2020 at 5:39 AM

It's still not letting big comments through, but I thought I'd ask about something. Have you heard from the school or the specialist about your "urgent" Friday meeting yet? You know, the one where he wants you to dress like a 10th Avenue whore for the receptionist?

(0) (0)

by nunya on Oct 22, 2020 at 5:43 AM

There's been more than one man ended up married to his "slump buster" - the woman that ends his sex drought. On the same vibe, many a wife got into the relationship because she was "dickmatized". From what I'm told, it doesn't even have to be an exceptional cock, it simply has to be available and used skillfully enough to give the lass regular orgasms.

Four.

(0) (0)

by Anonymous on Oct 22, 2020 at 5:50 AM

Going back to Monday's session, you took on both of them, gave the teacher some head, had several orgasms of your own, and ended up with four loads in you, I'd say it was a highly successful meeting. Pity the teacher can't get away more often so they both can use you together.

4

(1) (0)

by nunya on Oct 22, 2020 at 5:52 AM

I like that you revealed that you wanted to get fucked. It seems like you're finally investing in the experience, at least on a physical level. I wonder if seeing you get ass fucked, and feeling your mouth on his cock will give the teacher any ideas about expanding the weekend menu in the back of your car. Maybe he'll make going for two orgasms part of the program. Or cumming in your other holes. Given that you say about his erection during the second effort, he might content himself by getting blown while he plays with your tits for his second cum.

I note with no small amusement that the specialist got lost in the moment and commenced kissing you right after you gave the teacher head. It's a small thing in the grand scheme, but a lot of men won't kiss their partner after getting head from them - even if it isn't to completion. Very few will kiss a woman after watching her give another man's cock a tongue bath. Did he continue to kiss you while he was fucking your ass?

5

(1) (0)

by nunya on Oct 22, 2020 at 5:53 AM

Did it make you feel over the top slutty to ask the specialist to cum up your ass while you had the teacher as an attentive audience for your orgasm and debasement?

6

(1) (0)

by nunya on Oct 22, 2020 at 5:53 AM

In the aftermath, did you skirt have any distinct patterns from being rolled up under you on the floor while you were being debauched? Were there any obvious wet stains on it that were so low your jacket wouldn't cover them? Was the receptionist at her post? Is there any chance she or the principal, vice principal, etc. saw you leave?

7

(0) (0)

by nunya on Oct 22, 2020 at 5:54 AM

With three loads, could you feel the cum oozing down your inner thighs and leaving a shiny trail for all to see? If I read your storyline correctly, you cleaned your car seat before you showered and changed clothes. Did any neighbors get a chance to see the disheveled, leaking, "just fucked" you out there scrubbing on your car seat with a semen stain spreading across your skirt?

8 and last

(1) (0)

by Anonymous on Oct 22, 2020 at 9:27 AM

No need to wait for Friday, my second meeting with the specialist happened today. Quick details…I’m on the board of a non-profit helping kids, we had a breakfast get together at a hotel this morning. The specialist was there along with the school principal. I felt very uncomfortable realizing the specialist was there. I wasn’t dressed for a meeting but wasn’t really worried since this wasn’t a meeting after all. I still had a dress on with collared shirt underneath, but it went to my knees…and I had on a thong at least.

I sat at the front so didn’t have to talk with the specialist and principal until afterward. I said hello to them and they were both polite and professional. We talked a while then the principal said he needed to get going back to the school. They didn’t drive together…probably too early in the morning so they were coming from home like I was. No sooner than the principal leaves the specialist asks “So, where are you parked?” I told him “in the hotel lot” and he said “Let’s go over to the movie theater lot.” The movie theater is nearby but off to the side of the mall. Right now it’s closed.

I didn’t argue, just walked out to my SUV and the specialist got in the passenger seat. “Nice truck!” he said. We went to the movie theater and parked off to one side of the building. We were far from anyone, but at the same time we were just parked in the wide open lot. Anyone…mall security crossed my mind…could see us there. “Come on over” he said to me and gestured to his lap. He started undoing his pants. “People can see us.” I said. The front window and even front side windows aren’t nearly as dark tinted as the back. “So don’t make it take too long and no one will see.” he replied.

I hiked up my dress and slid my thong to the floor. I crawled over the console to him and straddled him in the seat. He reclined to get a better angle. I slowly worked down onto him, the first few strokes just to lube up then I could go down all the way. He grabbed at my breasts through my dress, but there was no way to get them out between my bra, the shirt underneath and the dress being zipped in the back. I started riding him pretty fast and he told me to slow down. “I thought you wanted it fast?” I asked and he said “Not too fast, it’ll be fine.” Easy for him to say…my SUV with my bare ass grinding up and down in the window. He pulled me down to him and we started kissing then he held me by my hips.

I think he lasted like 10 minutes before he came. I came with him but mostly I just wanted it over with. It felt good, but I was scared to death of being seen the whole time I couldn’t relax. I just kept picturing my ass in the front window going up and down…though I’m not sure how much you could see from outside, I pictured seeing it all. I climbed off, we got dressed, and I took him back to his car. “Monday?” he asks and I finally said “The more we meet the harder it is to sneak around.” He actually agreed, but then said “let’s do lunch!” So now we’re meeting for lunch on Monday.

It’s probably better that we not meet at the school, so maybe we’ll try this and it will be better. As for today, I ended up having to go to another appointment with my thong wet from sex and my dress all wrinkled from being bunched up again.

For your other questions:
Yes, my skirt was wrinkled on Monday. No you couldn’t see it because of my jacket. Yes, it might be obvious something is going on that I wear a jacket but have nothing on my legs. No one saw me cleaning my seat since I can park in the garage at home. I don't know if it was good or bad that my jacket and skirt were both too short to cover my ass when I sat in the car.

I didn’t feel slutty asking him to come in me, I just feel dirty when I get home and have to clean up. I much prefer him thinking this is just fucking rather than something serious so the kissing freaks me out. I don’t care about his personal life so I didn’t ask him anything. I know he’s single but that’s about it. I’m a little afraid of getting a STD but that’s about it, too.

I’m not going into detail about my son or my husband. I’ll just say that my husband is more traditional, straight-laced. He’s very good in bed and I guess you could say dominant. We don’t do too many nasty things. It’s a great marriage that I prefer not to mess up!

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by Anonymous on Oct 22, 2020 at 1:55 PM

So what's worse - being embarrassed walking into your kid's school in sexy outfits under a jacket or meeting at places where you might not be seen? At least at the school he has a job to lose. Outside of work he doesn't have any controls over him.

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by Anonymous on Oct 22, 2020 at 3:20 PM

Well, well, well. Did you forget a detail or have you not been told where your "lunch" date is?

As the Anon above me notes, there are fewer restrictions on his imagination outside of the school. Do you think it will have an impact on what he chooses to do, and how long he takes?

I'll also be curious to hear how long the encounter lasts. I doubt he'll have unlimited time to devote to using your sexy body to get his rocks off, but I also doubt he'll feel as rushed as he does at school.

Has he given you any indications of what to expect or how to dress? If I had to speculate, there will be substantially more kissing and fondling up front. I also predict that if he doesn't feel that you're sufficiently enthusiastic about returning his affections that you'll be in for a protracted anal pounding with as much gape as he can produce.

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by nunya on Oct 23, 2020 at 5:38 AM

Going back to your encounter with the teacher and specialist in the office Monday, you said "the orgasms were amazing" in reference to masturbating while the specialist was ass fucking you. Any guesses on how many there were in addition to the simultaneous one at the end?

Again showing just how much ego is involved for men who manage to make a woman orgasm, I admit some amusement that the teacher apologized to you for not being able to make your "appointment" at the parking lot on Saturday. It sounds like he expected you to be disappointed that he didn't show up to treat you like a 10th Avenue whore because you didn't get the one orgasm per week he contributes to your existence.

And thinking back to your adventure in the SUV, you said you managed to cum at the end. Was that also close to simultaneous? Did his orgasm trigger yours? Or did yours trigger him?

Was your thong enough to contain his load? When you got home and took off that wrinkled skirt, were there any traces of him visible on the back?

And just for the sake of saying, I've not asked for any information about your husband or son. That was someone else who opted to hop in and ask too personal questions. Beyond asking for your speculation on how long you might be in the clutches of the specialist, I've kept almost all of my questions and speculations in the "here and now" of your encounters with the two men debasing you for their own pleasure.

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by Anonymous on Oct 23, 2020 at 9:24 AM

I’m negotiating the next meeting by text. The specialist texted he wants to meet Monday or Tuesday and suggested we do it after school and that I make up an excuse that I have some shopping, or visiting someone, or charity work…something to tell my husband basically. It’s not just my husband, it’s also having my son picked up, watched, all that stuff. Plus I can't do that every week.

He wants to go somewhere we can have sex without having to pay too much. I suggested my SUV, but he texted back “Boring”. I can tell he’s trying to come up with a plan he can repeat. I said his condo and he said no, so I’m wondering if there is someone there…but I didn’t see any evidence of a girl in the condo. Right now his perverted mind came up with a “XXX Book Store” and I replied “Hell No”…he hasn’t replied back yet with anything else.

So getting really specific, I came twice while I fingered myself and then once more when he came in my ass. With the teacher, I try to hold off as long as possible, but it doesn’t always work. I get frustrated if he or anyone comes before I’m ready…I really like going together, but it doesn’t always work like that. I guess you’re a visual person, always asking how my clothes look after sex. No, the thong wasn’t big enough to catch everything since I was sitting down. It wasn’t much but a little got on the inside of the back of my dress.

The specialist texted back that the book store idea sounds really good to him. There’s no way I’m doing that, so I replied that I’d pay for a cheap hotel room if I had to. Couple of minutes he texted “OK” so now we’re going to some hotel Monday night now. He’s texting that I should check out the book store for an outfit, then sent a ROLF emoji…great…

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by Anonymous on Oct 23, 2020 at 10:10 AM

Monday night? Has he negotiated his way up to having access to your holes all evening?

All I can think to do is advise you to be VERY careful. No bondage games or blindfolds and definitely no bondage with a blindfold. It's the shortest route I can think of to you becoming a breathing sex toy slash porn star for him and some of his closest friends.

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by Anonymous on Oct 23, 2020 at 11:30 AM

I know, right?

I guess I'm not trying to sound like a "whore", but if it was just sex like it has been with the teacher, I could probably live with this almost indefinitely. I can convince myself the sex is just sex.

But now I'm on Darkest Hour Apparel (yes, first time on this one!). I'm looking at outfits as if it really matters what I buy. I've been thinking...what if he does something to my drink or something? The book store almost sounds safer, but then I'm worried he'll try to get me to blow some complete stranger or worse.

If he would have just been "normal" about it...just hooked up for some quickies or we planned a couple of rendezvous... I know I've jumped into this but I know this is not going to work like this.

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by nunya on Oct 23, 2020 at 12:58 PM

I'm looking at the Darkest Hour intimates. If you haven't already ordered something, knowing the specialist has a thing for easy access, and that you have [from your description] the body to carry it off, I'd suggest almost any of the lace teddies or the lace Melissa cami styles without any foundation garments. You know he's going to want see through fabric and the ability to bend you over and fuck you without any hassles like moving a thong out of the way.

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by nunya on Oct 23, 2020 at 1:12 PM

On the subject of your drink, I'd say you have a valid concern. He seems to have taken a liking to you physically, and anything he can do, perhaps including spiking your drink or slipping you a roofie, so he can insure his continued access to your toned body is on the table. Waking up from dru gged sleep uncertain if he has pictures and video of a zombified you servicing just him or several men is one way to blow everything sky high - or make you his personal sex toy until he tires of you.

Of course you can short circuit that by bringing your own sealed drinks. You don't have to be obvious about it. If he asks, just tell him you want to keep your head clear so you can enjoy the fucking.

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by Anonymous on Oct 25, 2020 at 6:10 AM

Did you have your weekly session in the SUV with the teacher yesterday? Did he go for two orgasms and blow his nut in your mouth on the second one?

If it was a straight up single pop fuck as usual, did he ask for head to warm him up first?

And I know I've asked before, but what position were you in for him to fill your married pussy?

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by Anonymous on Oct 26, 2020 at 11:05 AM

So what did you end up ordering from Darkest Hour?

I've been thinking about your earlier speculation and I think you're right. If you met him at the adult video place he would, with few doubts, take you back to the booths and search for one with a glory hole for you to service strangers through. The biggest danger there would be him secretly getting photos of you in a compromising position while you're occupied with sucking a cock through the hole. The same effect as the roofied drink - blackmail to keep you bound to him beyond any "payment" he could give you by aiding your son.

This is pretty early in the game, so he may be cautious for the moment, but I can't help but feel his long term plan is to either hook you emotionally - something you say isn't going to happen - or get you over a barrel to insure your continued compliance with his sexual demands. Did he give any reason for not meeting at his condo? I suspect your guess about there being a woman in residence may be correct. But it may also be him plotting something involving photos or video where he doesn't want his condo identifiable.

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by Anonymous on Oct 27, 2020 at 7:47 AM

I met the specialist at the hotel I paid for. I checked in wearing a long coat over my dress, but I’m sure the clerk and the two other people in the lobby saw the silver platforms I had on. I went out to the parking lot to wait in my SUV but the specialist was there waiting with two other guys. I wanted to run away, but they were at my car anyhow. I said I thought we were meeting alone and he said “Well, I told them all about you and they wanted to meet you.” That was b-s and he had a shitty grin on his face when he said it. He introduced me to them and I shook their hands.

We got in the room and I said “No pictures” then took off my coat. They started making comments and giving me compliments on my dress…a sequin mini dress (I got it from Revolve instead of that other site). There was some small talk but then they sat me on the bed. One guy started between my legs and started eating me out while the specialist asked if I wanted a drink. I know what we said about getting knocked out, but I took it anyhow and tried to relax while the guy worked between my legs. They guys drank too from the same bottle so I felt a little better. I started getting into it and all three of them commented how I was relaxing fast.

The guy giving me oral pushed me back on the bed and mounted me. The other two even told him to take it slow and we had time. He pushed off his pants and entered me anyhow, pulled down the top of my dress and started sucking my breast while he pumped away. The other two just watched. The guy on me pumped away for maybe five minutes tops then came in me while I orgasmed, but it wasn’t very strong. The specialist asked “What’s the rush?” and the guy on me said “I couldn’t help it, she’s hotter than you said.” I laughed a little out loud, the guy still going limp inside me.

The specialist helped me up and helped me take off my dress. The third guy said “Wow, even better without clothes.” I’ve seen better strippers and a couple of friends too, so I don’t know if they were just talking me up or if I really was the hottest they’ve ever seen…but it made me feel good.
I know I should now launch in to a step by step explanation of what we did. I don’t have the energy to do all that…I feel exhausted typing. I came a lot last night. I ended up with them coming in my puss three times, four bjs and anal one time with the specialist. I did “clean their shafts” this time, even if I blew them first and had sex later, but I asked to not clean off the specialist after anal and he said not to worry…that would be too gross. The last bj and the specialist in my ass were smaller than the other orgasms since they both had already gone twice. We were in the room nearly three hours, maybe over three hours. In between sex, I would make out with them…sometimes just one guy, other times two of them or one time even all three between kissing, my breasts and one guy even going down on my puss even after sex with another guy!

The guys were all circumcised and the specialist was the longest by a little bit. The third guy actually felt the best because he was a little thicker and he was the last one in my puss. This morning I actually feel a little empty and keep thinking about him. I fingered myself this morning after my husband left. I used two fingers which is unusual…I only use one for some light pleasure usually, or use my vibrator. I was too impatient to get it out of the drawer today.

I took a shower with the specialist while the other guys got dressed. We kissed a few times, but I also tried to talk to him about what is happening. We’ll get in trouble if we keep escalating. I told him I appreciate the help with my son. I made sure not to tell him that I’m starting to really enjoy the sex. I said I think we will get caught at school if I keep coming in dressed wild and he agreed saying the short jacket over top of bare legs wasn’t helping, especially with heel s a couple of times. He said the front office was commenting to him that I didn’t know how to dress appropriately and where does he look when I’m sitting in front of him. Great, I thought, another reputation I can’t live down.

The agreement is that every other week we will meet at the hotel. If the two guys are available, they’ll come too. I asked that he not bring more guys in and he said he wouldn’t promise that but that he would only bring two at a time and he’d be careful who he brought...no one from the school. On the “off” weeks I will still meet him at the school, but I can mix up my outfits so that I don’t keep drawing attention…no panties allowed, though.

On top of this I still see the teacher on Saturday mornings. I saw him on Saturday and we had our usual meeting. When we do it, most times I sit on the seat in the second row reclined back a little with my butt on the edge, we move the passenger seat all the way forward, and he kneels in front of me and then mounts me in the seat. Other times I sit or kneel on his lap while he sits in the same seat reclined.

And so far I think my husband does not know. I wore a change of clothes home last night, so he saw me in a normal outfit. He was watching football so I was fortunately in the clear for sex. I just checked on my son already in bed then went to bed myself. If I get home and he wants sex I’m not sure how it would go because I’m sure I feel different down there than if I hadn’t had any sex. I’d rather not find out. But for now, this could be my new routine so I’m still scared of being caught but I really do like the sex a lot. I feel slutty but I also feel really sexy and excited.

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by Anonymous on Oct 27, 2020 at 3:36 PM

I thought about this a lot today, and I feel younger doing all of this. It's stressful for sure, but I feel like I'm back in college. I wasn't the wildest, but the sorority I was in was pretty wild and we encouraged each other to be promiscuous. I think that's what excites me about my situation...it makes me feel like I'm back in college having fun, just this time there's this cloud in the background that I can push away while I'm doing it. I really hope I don't fuck this up :) but I think I can admit that I want it to happen...versus a week ago when I still felt more guilt than anything else.

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by Anonymous on Oct 28, 2020 at 10:05 AM

So I’m a big fan of you and your situation. I see that the specialist likes to continually escalate the situation with you. I wonder when this will blow up. I really hope it doesn’t for you. As a cuckold myself married to a woman who has cheated in almost every relationship she’s been in I told she just has to be safe and disclose everything to me. Would love to hear more about your promiscuous youth especially fucking black cocks

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by Anonymous on Oct 28, 2020 at 11:04 AM

Wow. Things have gotten even more complicated than the last time. Three guys is like the bare minimum for a gangbang, but since you were coaxing two or three orgasms out of each, your experience definitely qualifies. However, given that you had actual free time between rounds to cuddle and make out, don't be surprised if the specialist slowly raises the bar until you're servicing his whole seven man Thursday night poker group. They may not get as much individual attention, but they'll all be grateful to get at least one orgasm and a "shaft cleaning" from the pretty woman with the nice tits and trimmed bush.

I have to ask, with what you said about your sorority "encouraging promiscuity", is three the most men you've entertained on one session? Does three tie you high water mark? Is it a new personal record? Or is there some slutty evening in your early twenties that exceeds it?

After you started giving head, including head after fucks, did they continue to kiss you on the mouth? Speaking of such, I know you said you took a change of clothes with you, but did you take a toothbrush and paste or mouthwash with you so you wouldn't have cock breath when you got home?

My imagination runs wild at the potential combinations of you and three men. However, it sounds like the specialist is trying to keep your ass as his exclusive property, though he was nice enough to let one of his compatriots have your mouth at the same time. You say you asked to not have to clean the specialist after he fucked your ass. What would you have done if he had said he expected you to? Would you [pun intended] suck it up give his dirty cock a tongue bath?

Thinking of the shaft cleaning for a minute, who initiated that? Was it something one of the new guys or the specialist requested after leaving a load in your c**t? Or was it something you initiated because you were feeling extra slutty?

Coming back to the practical for a minute, I like that you're only going to have to see the specialist at school every two weeks and that you get to dress more conservatively for it. I do question you having to come up with an excuse every two weeks to get away for four or five hours, not to mention having to pay for a room every two weeks. Even the no tell motel locally that the hookers are said to frequent go for $35 or $40 plus fees and taxes. I know you said your husband does well, but an extra $120 or $160 a month [plus taxes and fees] in expenses that keeps repeating would get noticed in my place and credit card bills checked. While it may sound more "whorish" to you, you may have to tell the specialist that he and his companions that come by to get their nuts drained need to at least cover the cost of the room.

The commenter that got in before me raises some questions that seem entertaining, but I'd like to start earlier if you don't mind. I'd love to know the age and circumstances when you lost your virginity. And like the previous writer, it would be interesting to know about your promiscuous explorations as a sorority girl. How many frat boys got into your pants? Was it one of them that first opened up your ass for fucking? Did any of them DP you? Any interracial encounters back then? What is the largest cock you've ever serviced?

I see you list as straight, but based on your reaction to the question about servicing a woman teacher on a weekly basis I have to ask about those possible experiences.

Based on stories I heard from some of the sorority chicks back in school many years ago, did you ever dip your tongue in a well used pussy? [There was a rumor, vaguely affirmed by one of the afore mentioned chicks, that one of the hazing rituals of the day included orally cleaning both the boy and the girl from a fresh fuck with mouth and tongue. And another that involved underclass sisters who didn't have a date on a Saturday night providing cleaning service to the upper class ones who did.] Or, at a somewhat lesser level, was there straight up exploration with one of your sister just to see what it was like?

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by nunya on Oct 28, 2020 at 12:21 PM

That's me in the long comment above. I had a few more random thoughts to get down before I forget them.

First off, I know you went clothes shopping before your excursion. Is that going to be a regular thing as well? Does he want you in new slut wear every two weeks? At first it might be something you can pass off as a whim to your husband - sexy clothes to help get him in the mood. But over the course of a few months you could build up enough to put a whore or stripper to shame. I don't have a solution, but it might be something to discuss with the specialist. Other items in your wardrobe seem to have been enough for him before and the others haven't seen them, so maybe you could repeat the outfits provided nobody rips them off of you.

Again, and I repeat myself for emphasis, no bondage and no blindfolds. It is now a given that he's bringing along other guys to fuck you now, and if there is any moment where you're exposed or busy with a cock but can't see, you have to assume there is a camera recording your actions. And of course with bondage, you've just ripped off any upper limit to the cocks you'll service on a particular night. And being blunt, claiming r**e won't help if you've been observed there with groups of men before - it simply makes you an unpaid whore. If there are no bruises and there are orgasms, there's no r**e in far too many places.

If I assume you smarter than the average hooker, you managed to pay in cash. Did they insist on credit card and license plate numbers to insure against loss? Even taking care, will you be easy to track? Was the SUV near the motel office where the night guy might see you go to the room with three men?

And circling back around for a minute to the two new guys, did anyone wear a condom? Or did all three dump their loads without a care in your mouth and married pussy?

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by Anonymous on Oct 28, 2020 at 3:07 PM

Lots of follow-up…I guess I expected that! I’ll try to go in order but not write too much of a novel.

Will this blow up? Probably…in my mind I’m saying “Like, yeah it will.” I’m hoping to calm everything down so we get in a rhythm. Let’s chill a while instead of always adding more. If we can do that, I think this can go on for a while at least…maybe he’ll even get bored, or at least treat it like a scheduled appointment like the teacher does.

So, college was great. I wasn’t a virgin when I got to college, but had only been with a few guys (five). By the end of my junior year I had been with about 40 more (not being modest …even my husband has a “rounded” number…less than 20 total) Anyhow…it started with pledging the sorority. I’ve been with most races I think…size varies but I seen all sizes I think. There was a black guy we called Monster behind his back…he was hard to take, I was with him a few times but never really enjoyed it. I didn’t have to clean anyone’s shaft involuntarily, but that happened because I did a MFF threesome and cleaned him after he had sex with my sister (sorority sister…). I’ve watched other girls clean me off of guys too. I did a few MMF threesomes, usually during or after parties at the house on a Saturday night or at a frat house. College is where I first had anal. I had never done MMMF until the specialist…but I did MMFF or however you’d say that. I ate puss while getting fucked. I did DP two times in college with different guys. I guess I don’t consider it being bi because it was just messing around in college. I don’t secretly lust after any of my friends now, but I guess if one kissed me I’d have no problem kissing back.

Funny thing…I don’t think the three guy thing came up in college because there were usually enough girls in the house to cover threesomes…foursome would’ve wasted drinking time!

When I met my husband it all changed pretty quick. I was still partying when I first met him, but when we decided to officially date, that is when it stopped. He wasn’t involved in the dirty stuff, but kind of rescued me if that’s the way people look at it. I had to put it in the past and settle down. My grades went up slightly, so I should’ve done a little better in college. To put it bluntly, my husband is a control freak and somewhat traditional. If he found out I’m doing this, I’d be more worried about losing fingers, arms or legs than I would worry about divorce. Not that I’m breaking my rule about talking about my family, but maybe that helps steer you to what he’s like without being too specific.

Back to the new questions… A week ago I didn’t think about multiple partners at the same time, so all I can say is I hope it stays like this now. Not to be a rich b*tch (not sure if that filters…), but I’m okay paying the hotel. I can just say I don’t have to worry about my cards being audited, and cash is there too.

Why did I clean their shafts? I got into it. It was more like they were coming to me for a bj and I just took them even after they were in me. Oral after anal would be nasty…the lube and the crap? Yuck! I think that would ruin it for everyone. On the last question…mouthwash, gum, and a drink on the way home.

I know it’s a real risk, but there were no condoms. Even in college I was hit and miss on condoms. I really don’t like them. I know you can’t tell if a person has something by looking, but I guess I try not to worry too much. The specialist bringing more guys did make me think about it.

Clothing…no I won’t buy a new outfit every time…I have a few outfits that I could wear but some of them are the really short schoolgirl skirts you can’t wear in public, Halloween outfits, things like that. Plus some of my everyday clothing is pretty short just because of my size and height. It’s horrible now that I’m typing it, but I bought this dress thinking my husband would like it too…so now I’m thinking maybe I shouldn’t do that but the dress was expensive. It’s really short, but it’s the kind of dress I could wear to a super trendy restaurant or a New Year’s party and get away with it. It feels slutty (in a good way) to think I’d be at a party with my husband and friends in a dress I already used for secret sex.

Sneaking around might get tough, but I am the girl with a million causes. I said early that I needed to volunteer to be social. So me going to meetings is pretty normal. It’s a variety of things, but so long as it’s not every single night, I can do it.

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by Anonymous on Oct 31, 2020 at 8:16 AM

Did your husband know about your promiscuous ways before you started dating? Did he fuck you at one of these parties before you two dated?

If you didn't enjoy Monster the first time, why did you go back for more? I think the thing I'm really curious about is whether he truly tried to make it good for you. I recall one woman who confessed she had been with our college's equivalent to Monster and she said he was so in love with his dick that as long as she was a willing hole for him to get off in, he didn't care much about foreplay or her enjoyment. She said it was like being in a really bad porno where there was an almost constant commentary about how big he was and how his big black cock was going to always be the biggest thing in her pussy until she gave birth.

I'll go ahead and ask, even though the door was supposed to close for the week after the gangbang, was the specialist in contact with you again during the week, hoping for a late week office hookup? You know that may be something that eventually comes to pass, even with this "agreement" you have. If you suddenly go from one or two in office meetings per week to one every two weeks, he may end up getting questions about what has changed. It sounds like you may have one or two fans of your ass and legs on staff who look for you and will notice if you don't show. Something to think about. As the weather gets cooler and your dresses more conservative, you may have to make a few late week visits on hotel weeks to give him a quick blow job and actually talk about your son for a short while.

I don't know how much of a concern condoms are at this point. Assuming the specialist's friends are married or at least in some form of committed relationship and you're the only outside pussy they're sampling, the risk should be fairly low. If the specialist suddenly becomes concerned about safe sex, follow his lead and assume one of the people he brought along may be problematic.

Going back to the gangbang logistics for a moment, did all of the action take place on the bed or did you end up on your knees in floor giving head to multiple men in a circle?

Were all three of the men you were with Monday white? I know you said the specialist was the longest by a hair and the third guy had a nice thick cock. How do they compare to your husband's equipment?

I know you're scheduled for the teacher today. Let us know if he changes anything about the routine. Having felt your mouth on his cock and seen you clean the specialist after he fucked you, it would not take a great leap of imagination to think he'll ant shaft cleaning and a chance to empty his nuts in your mouth after a preliminary fuck.

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by Anonymous on Nov 2, 2020 at 1:27 PM

Saturday and today were pretty much as you would expect both. The teacher and I talked during sex, mainly about my experiences with the specialist. The teacher didn't ask for anything more form me, but he did get, I think, more excited than usual and had a very strong orgasm when he came. He did ask if we used condoms at the hotel...when I said we didn't, I think it made him hornier...

I have to admit, these conversations have me thinking of asking to give the teacher a bj. I love him in my puss, I really do, but now I've been thinking about his penis in my mouth...I do like giving bjs.

The session with the specialist had to be quick today, so now that I'm allowed to wear pants it was a quick "roll down your jeans" quick screw me from behind. It felt good but it was so fast it didn't feel worth the sneaking around. Like you said, he's asking for more and this time he wants to meet Thursday or Friday but it has to be during his lunch. He basically told me to bring my SUV and be ready to make the most of his lunch hour.

So somewhat ho-hum this time. Sorry!

From last week's hotel romp, they were all white and close to my husband in size. Well, the specialist and the "third guy" are probably a little bigger. I was on my knees for two of the blowjobs, on the bed for the others. One of them was laying down while I was between his legs, the other one was sitting on the bed while I was getting fucked form behind by the other guy.

My husband knows I partied in college, but he wasn't part of that crowd. My sisters were actually very discrete about what I did before I met him and we sort of play it off like I was always the good girl...which I sort of was in comparisons to my closest friends!!!

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by nunya on Nov 3, 2020 at 6:52 AM

If you like the teacher and have a desire to blow him, have you thought about offering to clean his shaft after the fuck and then extending that out to a full blow job? You get your orgasm from the fuck but still get to give him head and see how he tastes. Of course, the downside is that he might enjoy it so much that he'll want it that way every time.

Sorry you didn't get your usual orgasm from your encounter with the specialist. Did he seep out and discolor your jeans?

Oh, did the bitch still stare knives at you when you checked in even though your clothes were more conservative?

I wonder if things might be related in an odd way. Maybe showing up in slutwear and getting her disapproving look is one of your triggers to get turned on for the specialist, even if there is an element of humiliation involved. Forcing you to show up commando in your "I'm getting fucked" dress sounds like it's a turn on for both of you. You feel young and sexy and he sees you as his personal whore. In jeans you revert to MILF status and the fucking gets more mechanical.

You might test the theory later this week by dressing trashy for your noon quickie. If you can just text him that you're in the lot and let him have a good look at those shapely legs and a decent feel while you drive to whatever out of the way place you go to do the deed, you'll get a chance to observe both of your excitement levels.

Since you've answered about the guys at the gangbang I'll ask about the last of the group. How does the teacher compare to your husband and the specialist in the cock department?

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by Anonymous on Nov 3, 2020 at 1:22 PM

I think I will give the teacher oral this weekend. Whether it's before or after sex, I'm not sure. I'm okay with after, but we'll see what happens. I've been thinking about it and want to try it with him. At this point, it's not like a bj is any boundary or over some limit.

My jeans did have a wet streak on them from sex with the specialist. I did go to coffee afterward, but you had to look right between my legs with my legs spread to see it. I do wonder if he's juicier because he's younger maybe?

I will be dressing up for Thursday, so we'll see how that goes, too. The meeting on Monday was rushed so I think it had more to do with his schedule than anything else. I think Thursday is a re-do because he couldn't take time on Monday. Plus it's probably like you said...he's getting in more visits this way.

The teacher isn't circumcised and I think that feels different but not really bigger. I think the specialist is longer.

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by Anonymous on Nov 3, 2020 at 5:41 PM

Appreciate the updates on this thread. I did have a question about your encounters. As this has seemed to go on for a couple weeks, how are you handling your time of the month? Or are you just going for it?

In a different context, are you fantasizing about your encounters throughout the week, or just right before your encounters? Do you think about sex with the specialist and teacher while having sex with your husband?

To your discussion about outfits, are you planning way in advance for each encounter or just deciding day of?

Best of luck. I think this will probably blow up in your face, but you are your own adult and can make your own choices. Cheers.

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by Anonymous on Nov 4, 2020 at 12:46 PM

I get a Depo shot so there's some spotting from time to time but most of the time nothing. It's absolute awesome, though eventually I'll have to switch off.

At first I blocked out as much as I could, but the more I started to think about it the more I thought about the sex I'm getting. That was a few weeks in and around the time I originally posted. Since then I've tried to convince myself it is just sex. I don't care if it's the specialist or the teacher right now, but I want it and the hotel night sealed the deal. Like I really want the sex now.

I did plan my outfit for Thursday already. I'll wear a loose off the shoulder top and a denim mini with the buttons down the front. I have to pick out shoes or boots yet.

I know it can't last like this forever. I know I need a plan but right now I don't have one.

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by Anonymous on Nov 6, 2020 at 7:06 AM

Yesterday went pretty well. The sex with the specialist was amazing and he came in me twice. I didn’t have a stain on my skirt :) but I did have a wet spot on the seat of my car again. The outfit was the short denim skirt and a regular t-shirt, with bra. The skirt starts at my belly button but only barely covers my ass, so I only wore it a few times for my husband but never out of the house until now. The specialist definitely approved when he saw me and it was perfect for sex since we couldn’t really undress.

We met at an old strip mall in a not so nice area. I thought we would go somewhere from there but instead he had me back my SUV up against the side of the building at one end. There weren’t many cars around, but I thought we sort of stuck out a little. He had me put down all the seats and we climbed in back. This time we kissed for a couple of minutes while he fingered me. Then he had me lie down and he mounted me…we were both dressed except he had his pants down his thighs. He started slow at first then slowly got faster and harder. Towards the end he had my feet up by my head as he got on his knees and pounded me hard. I came twice before he finished and then came again when he finished.

We laid in the back of the SUV kissing for a few minutes while he rubbed my bare ass after my skirt had ridden up. I played with him semi erect until he started to come back to life a little more. I was half afraid he wanted anal and I wasn’t in the mood for it…instead he had me get on top of him then come back down and kiss some more. We went slower and he told me I was beautiful and he loves watching me have sex and stuff like that. He asked me if I liked the experience with three guys in the hotel room and I didn’t think…I said “I loved it, I loved getting fucked by everyone!”

He lost control the second I said that and had a huge orgasm in me. It felt really strong considering he had just came 10 or 15 minutes ago. As he started to slow down and his erection came down he asked me more questions about it and if I’d do it again and if I’d do it every week. I said I could make excuses to do it like I was volunteering, but I couldn’t be gone for hours every week. We started working out how I could say I was volunteering somewhere and some weeks had meetings for a group I volunteered with. That would get us several weeks anyway…then we’ll have to see what happens.

He finally admitted he has a girlfriend. She is serious enough that she has a key to the condo but doesn’t live there full time yet. I asked how the sex was and he said “Good, but not at all like you.” The good news is that he intends to get engaged at some point, but is saving for the right ring and a bigger place to live.

The only thing we’ll do differently next time is find a better spot to park, but this time was exactly how I want it. Great sex and we go our separate ways when it’s over. I did tell him I’m willing to do the three guys on Monday nights if he wants and he said okay. Plan on Monday nights in a hotel…he’ll pay some and I will pay for others…and Thursday lunchtime we’ll find a good place to park and hook up. Plus I still have the teacher on Saturday mornings, so it’s a lot of sex and sneaking around, but fortunately my husband is busy enough he won’t notice and my son’s all set.

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by Anonymous on Nov 6, 2020 at 9:37 AM

Glad to hear your Thursday went so well and you had multiple orgasms. Was there any suggestion by him or you that you clean his shaft when you finished so he wouldn't go back to work with his cock marinating in your combined juices?

So, no playing at work now? No more inspections by the check in bitch?

Am I following it right, and instead of motel one week and office meetings the next, you'll be having a small gangbang every Monday at the no tell motel and one on one car sex with the specialist on Thursday or Friday?

I thought the plan was a fairly anonymous gangbang every other Monday and sex with just the specialist on the off week. Will being gone for three or four hours every Monday eventually pierce your husband's preoccupation with his job?

If you and the specialist are in the mood for anal come Monday, are you going to encourage one of the other random cocks to fill your pussy at the same time?

Did you and the specialist have any more discussion about your limits? Did you reinforce the notion that him and two others was it, or will he take your enthusiasm for getting fucked by multiple men as a signal to add one or two more to the crew?

Turning attention to the teacher for a minute, have you decided whether you're going to try to get him to accept a slow, sloppy blow job as a substitute for getting to drain his balls in your pussy or if you're just going to let him have his usual piece, then offer to clean his shaft, work that into a full blow job and try to get a mouthful of his cum before you quit?

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by Anonymous on Nov 6, 2020 at 9:57 AM

Glad you got some clarification on where things stand, not to mention some awesome sex! And thanks for sharing your adventures... I am obviously not alone in the dept judging from all the other comments.

You've done a great job with juicy descriptions... would you ever be open to sharing more, like perhaps a pic of you or perhaps a lookalike just so I (and many others I am sure) can visualize your adventures even better? :)

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by Anonymous on Nov 6, 2020 at 5:48 PM

I second the request for a pic or lookalike (or face blurred out and no identifying information). You have amazing descriptions and great details but a visual would be the icing on the cake.

One question: have you thought of introducing toys to the equation yet? Or is your current makeup good enough?

And does knowing he has a girlfriend make you more or less excited?

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by Anonymous on Nov 8, 2020 at 11:23 AM

I don't know if you read the comments first, but if you do, I was wondering if you could be persuaded to start a "new" confession with your thoughts about the situation, your activities with the teacher on Saturday, and a reference back to this confession (#47546) for those keeping track. I know it seems frivolous, but it appears the system has a hard limit of 50 comments. The tracker says there are currently 89 comments on your adventures in education, but the first 39 have been zapped. It makes it really hard for the newcomers to play catch-up when about 44% of the comments have been memory holed.

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by Anonymous on Nov 10, 2020 at 9:17 AM

Did you have your scheduled gangbang with the specialist last [Monday] night? How many men did he bring along? Were they the same as the last time or did he switch things up? How long did it take and how many loads did they leave in you?

Did you get double penetrated [pussy and ass at the same time]?

How was your meeting with the teacher? Did you get a mouthful of his married cum? Was he your first uncircumsized cock?

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by Anonymous on Nov 10, 2020 at 12:29 PM

Based on the last couple of comments, I posted the latest as 47991.

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